New reactivity of 6,6-bis-donor-substituted pentafulvenes: one-step synthesis of highly substituted [3]cumulene and dihydropentalene
We report the preparation of a 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene from a 6,6-dibromopentafulvene and 4-ethynyl-N,N-dimethylaniline under Sonogashira cross-coupling conditions. A push–pull [3]cumulene was formed unexpectedly during this reaction in moderate yield. The 6,6-bis[(4-N,N-...
Saved in:
| Published in | Tetrahedron Vol. 71; no. 25; pp. 4393 - 4399 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
OXFORD
Elsevier Ltd
24.06.2015
Elsevier |
| Subjects | |
| Online Access | Get full text |
| ISSN | 0040-4020 1464-5416 |
| DOI | 10.1016/j.tet.2015.03.081 |
Cover
| Abstract | We report the preparation of a 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene from a 6,6-dibromopentafulvene and 4-ethynyl-N,N-dimethylaniline under Sonogashira cross-coupling conditions. A push–pull [3]cumulene was formed unexpectedly during this reaction in moderate yield. The 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene was reacted with tetracyanoethylene, and an unprecedented 1,2-dihydropentalene was obtained in high yield as the exclusive product. The structures of the new compounds are supported by X-ray analysis, and a reasonable mechanism for their formation is proposed. We also report their interesting opto-electronic properties, as studied by UV/vis spectroscopy and cyclic voltammetry (CV).
[Display omitted] A 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene has been prepared using a 6,6-dibromopentafulvene and 4-ethynyl-N,N-dimethylaniline under Sonogashira cross-coupling conditions. A push–pull [3]cumulene was formed unexpectedly during this reaction in moderate yield. The 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene was reacted with tetracyanoethylene, and an unprecedented 1,2-dihydropentalene was obtained in high yield as the exclusive product. |
|---|---|
| AbstractList | We report the preparation of a 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene from a 6,6-dibromopentafulvene and 4-ethynyl-N,N-dimethylaniline under Sonogashira cross-coupling conditions. A push–pull [3]cumulene was formed unexpectedly during this reaction in moderate yield. The 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene was reacted with tetracyanoethylene, and an unprecedented 1,2-dihydropentalene was obtained in high yield as the exclusive product. The structures of the new compounds are supported by X-ray analysis, and a reasonable mechanism for their formation is proposed. We also report their interesting opto-electronic properties, as studied by UV/vis spectroscopy and cyclic voltammetry (CV).
[Display omitted] A 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene has been prepared using a 6,6-dibromopentafulvene and 4-ethynyl-N,N-dimethylaniline under Sonogashira cross-coupling conditions. A push–pull [3]cumulene was formed unexpectedly during this reaction in moderate yield. The 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene was reacted with tetracyanoethylene, and an unprecedented 1,2-dihydropentalene was obtained in high yield as the exclusive product. We report the preparation of a 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene from a 6,6-dibromopentafulvene and 4-ethynyl-NN-dimethylaniline under Sonogashira cross-coupling conditions. A push pull [3]cumulene was formed unexpectedly during this reaction in moderate yield. The 6,6-bis [(4-N,N-dimethylanilino)ethynyl]pentafulvene was reacted with tetracyanoethylene, and an unprecedented 1,2-dihydropentalene was obtained in high yield as the exclusive product. The structures of the new compounds are supported by X-ray analysis, and a reasonable mechanism for their formation is proposed. We also report their interesting opto-electronic properties, as studied by UV/vis spectroscopy and cyclic voltammetry (CV). (C) 2015 Elsevier Ltd. All rights reserved. We report the preparation of a 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene from a 6,6-dibromopentafulvene and 4-ethynyl-N,N-dimethylaniline under Sonogashira cross-coupling conditions. A push–pull [3]cumulene was formed unexpectedly during this reaction in moderate yield. The 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene was reacted with tetracyanoethylene, and an unprecedented 1,2-dihydropentalene was obtained in high yield as the exclusive product. The structures of the new compounds are supported by X-ray analysis, and a reasonable mechanism for their formation is proposed. We also report their interesting opto-electronic properties, as studied by UV/vis spectroscopy and cyclic voltammetry (CV). |
| Author | Guillemin, Jean-Claude Kerisit, Nicolas Trolez, Yann Diederich, François Leroux, Yann R. Finke, Aaron D. Trapp, Nils |
| Author_xml | – sequence: 1 givenname: Nicolas surname: Kerisit fullname: Kerisit, Nicolas organization: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France – sequence: 2 givenname: Aaron D. surname: Finke fullname: Finke, Aaron D. organization: Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093 Zurich, Switzerland – sequence: 3 givenname: Nils surname: Trapp fullname: Trapp, Nils organization: Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093 Zurich, Switzerland – sequence: 4 givenname: Yann R. surname: Leroux fullname: Leroux, Yann R. organization: Institut des Sciences Chimiques de Rennes, CNRS, Université de Rennes 1, UMR 6226, Campus de Beaulieu, 35042 Rennes Cedex, France – sequence: 5 givenname: Jean-Claude surname: Guillemin fullname: Guillemin, Jean-Claude organization: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France – sequence: 6 givenname: Yann surname: Trolez fullname: Trolez, Yann organization: Ecole Nationale Supérieure de Chimie de Rennes, CNRS, UMR 6226, 11 allée de Beaulieu, CS 50837, 35708 Rennes Cedex 7, France – sequence: 7 givenname: François surname: Diederich fullname: Diederich, François email: diederich@org.chem.ethz.ch organization: Laboratorium für Organische Chemie, ETH Zurich, Vladimir-Prelog-Weg 3, 8093 Zurich, Switzerland |
| BackLink | https://univ-rennes.hal.science/hal-01141537$$DView record in HAL |
| BookMark | eNqNkktv1DAUhS3USkwLP4BdliDqYOfhZGBVjYAijdpNWSFk-XFDPMrYg-1MlT0_HIeMKsSiwhtLV-c7uj4-F-jMOgsIvaIkp4Syd7s8QswLQuuclDlp6TO0ohWrcF1RdoZWhFQEV6Qgz9FFCDtCCKVFuUK_buEh8yBUNEcTp8x1GbtiWJqAtbPO4zDKEE0cI-jsADaKbhyOYCG8z9IGOEQ4ZGGysYdgwoz35kc_TNnf3Lfyuxr345CwTFidadNP2rs_dvPwBTrvxBDg5em-RF8_fbzf3ODt3ecvm-stVnVVRqwka0ULUgvaEVZAReuGrkndFqpZl-v0Hi2hVaDrppMFqGpNJZCuahspu0ZDeYneLL69GPjBm73wE3fC8JvrLZ9nKZRkWjZHmrSvF-3Bu58jhMj3JigYBmHBjYEXKcKioYwVSfp2kT6AdF1QBqyCR_-kK2tG05lDr5O6_X_1xkQRjbMbN9qYULqgyrsQPHSPGCV8rgHf8VQDPteAk5KnGiSm-YdRJ8_ohRmeJD8sJKQvORrw_LSsNh5U5NqZJ-jfm5zPTg |
| CitedBy_id | crossref_primary_10_3762_bjoc_20_13 crossref_primary_10_1016_j_comptc_2018_09_005 crossref_primary_10_1002_ejoc_201501085 crossref_primary_10_1002_anie_201711605 crossref_primary_10_1002_chem_201700043 crossref_primary_10_1021_acs_jpcc_8b05661 crossref_primary_10_1021_acs_jpca_9b02962 crossref_primary_10_1002_ejoc_201800039 crossref_primary_10_1021_acs_macromol_8b00977 crossref_primary_10_1002_asia_201700353 crossref_primary_10_1002_chem_202103079 crossref_primary_10_1002_chem_201703903 crossref_primary_10_1002_ange_201711605 |
| Cites_doi | 10.1021/ja00067a039 10.1021/om00135a015 10.1039/c2ob26028j 10.1021/jo402440m 10.1002/chem.201003628 10.1002/chem.200701981 10.1039/c1cc10247h 10.1002/anie.201304767 10.1002/asia.201100997 10.1039/p29930000911 10.1002/anie.197008922 10.1016/S0040-4039(01)96624-9 10.1021/ja983537+ 10.1021/ol502675n 10.1039/B417393G 10.1002/asia.201200179 10.1039/b821230a 10.1002/chem.201102852 10.1002/chem.201302452 10.1002/anie.201208058 10.1021/ja309141r 10.1021/ja045729c 10.1246/cl.2004.1190 10.1039/c3ob42574f 10.1021/jo302047m 10.1002/anie.198703351 10.1021/ol102384k 10.1039/b204168e 10.1002/chem.200700362 10.1039/c39830001529 10.1002/chem.201402653 10.1002/anie.201402299 10.1002/anie.199525891 10.1016/S0040-4039(00)88044-2 10.1021/nn301851k 10.1002/tcr.201402060 10.1016/S0040-4039(00)60777-3 10.1021/jo101634v 10.1107/S0567740877011819 10.1021/ja312084s 10.1039/b417393g |
| ContentType | Journal Article |
| Copyright | 2015 Elsevier Ltd Distributed under a Creative Commons Attribution 4.0 International License |
| Copyright_xml | – notice: 2015 Elsevier Ltd – notice: Distributed under a Creative Commons Attribution 4.0 International License |
| DBID | AAYXX CITATION 17B 1KM BLEPL DTL EGQ GVOUP 7S9 L.6 1XC VOOES |
| DOI | 10.1016/j.tet.2015.03.081 |
| DatabaseName | CrossRef Web of Knowledge Index Chemicus Web of Science Core Collection Science Citation Index Expanded Web of Science Primary (SCIE, SSCI & AHCI) Web of Science - Science Citation Index Expanded - 2015 AGRICOLA AGRICOLA - Academic Hyper Article en Ligne (HAL) Hyper Article en Ligne (HAL) (Open Access) |
| DatabaseTitle | CrossRef Web of Science AGRICOLA AGRICOLA - Academic |
| DatabaseTitleList | Web of Science AGRICOLA |
| Database_xml | – sequence: 1 dbid: 1KM name: Index Chemicus url: https://proxy.k.utb.cz/login?url=https://www.webofscience.com/wos/woscc/search-with-editions?editions=WOS.IC sourceTypes: Enrichment Source Index Database |
| DeliveryMethod | fulltext_linktorsrc |
| Discipline | Chemistry |
| EISSN | 1464-5416 |
| EndPage | 4399 |
| ExternalDocumentID | oai_HAL_hal_01141537v1 000356111100015 10_1016_j_tet_2015_03_081 S0040402015004056 |
| GrantInformation_xml | – fundername: French Ministry of Higher Education and Research – fundername: Swiss National Science Foundation and the ERC; Swiss National Science Foundation (SNSF) grantid: 246637 |
| GroupedDBID | --- --K --M -DZ -ET -~X .~1 0R~ 123 1B1 1~. 1~5 4.4 457 4G. 53G 5RE 5VS 7-5 71M 8P~ 9JM 9JN AABNK AACTN AAEDT AAEDW AAIAV AAIKC AAIKJ AAKOC AALRI AAMNW AAOAW AAQFI AARLI AATCM AAXUO ABFNM ABGSF ABJNI ABMAC ABPPZ ABUDA ABYKQ ABZDS ACDAQ ACGFS ACNCT ACRLP ADBBV ADECG ADEZE ADUVX AEBSH AEHWI AEKER AENEX AFKWA AFTJW AFXIZ AFZHZ AGHFR AGUBO AGYEJ AHHHB AIEXJ AIKHN AITUG AJBFU AJOXV AJSZI ALCLG ALMA_UNASSIGNED_HOLDINGS AMFUW AMRAJ AXJTR BKOJK BLXMC CS3 DOVZS DU5 EBS EFJIC EFLBG EJD EO8 EO9 EP2 EP3 F5P FDB FIRID FLBIZ FNPLU FYGXN G-Q GBLVA IHE J1W K-O KOM M2Z M41 MO0 N9A O-L O9- OAUVE OGGZJ OZT P-8 P-9 P2P PC. Q38 RNS ROL RPZ SCC SDF SDG SDP SES SOC SPC SPCBC SSK SSP SSU T5K TN5 TWZ WH7 XPP XSW YK3 YR2 ZMT ~G- .GJ 186 1RT 29Q 6TJ AAHBH AAQXK AATTM AAXKI AAYJJ AAYWO AAYXX ABDPE ABEFU ABXDB ACBNA ACKIV ACLOT ACNNM ACRPL ACVFH ADCNI ADMUD ADNMO ADVLN ADXHL AEIPS AETEA AEUPX AFFNX AFJKZ AFPUW AGQPQ AGRDE AIGII AIIUN AKBMS AKRWK AKYEP ANKPU APXCP ASPBG AVWKF AZFZN CITATION EFKBS FEDTE FGOYB HMS HVGLF HZ~ MVM NEJ OHT PVJ R2- SCB SEW UQL WUQ XOL ZCG ZKB ~HD 17B 1KM AGCQF AGRNS BLEPL DTL GROUPED_WOS_SCIENCE_CITATION_INDEX_EXPANDED GROUPED_WOS_WEB_OF_SCIENCE 7S9 L.6 1XC VOOES |
| ID | FETCH-LOGICAL-c543t-cb68a8ebda1f062e4157190582c7939123dbe8ced57fb2ec491be0f487bbf7de3 |
| IEDL.DBID | .~1 |
| ISICitedReferencesCount | 12 |
| ISICitedReferencesURI | https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=CitingArticles&UT=000356111100015 |
| ISSN | 0040-4020 |
| IngestDate | Fri Sep 12 12:43:50 EDT 2025 Sun Sep 28 01:32:18 EDT 2025 Fri Sep 26 20:43:33 EDT 2025 Wed Aug 06 15:33:56 EDT 2025 Wed Oct 01 00:40:50 EDT 2025 Thu Apr 24 23:03:05 EDT 2025 Fri Feb 23 02:33:49 EST 2024 |
| IsDoiOpenAccess | true |
| IsOpenAccess | true |
| IsPeerReviewed | true |
| IsScholarly | true |
| Issue | 25 |
| Keywords | Electrocyclization Cumulene [2+2] Cycloaddition Pentafulvenes dihydropentalene CUMULENES BENZENE MONO PUSH-PULL CHROMOPHORES X-RAY ACCESS SEQUENTIAL 2+2 CYCLOADDITION ELECTRONIC-STRUCTURE |
| Language | English |
| License | Distributed under a Creative Commons Attribution 4.0 International License: http://creativecommons.org/licenses/by/4.0 |
| LinkModel | DirectLink |
| LogoURL | https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg |
| MergedId | FETCHMERGED-LOGICAL-c543t-cb68a8ebda1f062e4157190582c7939123dbe8ced57fb2ec491be0f487bbf7de3 |
| Notes | ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
| ORCID | 0000-0002-5421-9556 0000-0003-2492-2678 0000-0002-4737-9922 0000-0002-6842-1122 |
| OpenAccessLink | https://univ-rennes.hal.science/hal-01141537 |
| PQID | 2000271662 |
| PQPubID | 24069 |
| PageCount | 7 |
| ParticipantIDs | crossref_citationtrail_10_1016_j_tet_2015_03_081 crossref_primary_10_1016_j_tet_2015_03_081 proquest_miscellaneous_2000271662 webofscience_primary_000356111100015 elsevier_sciencedirect_doi_10_1016_j_tet_2015_03_081 hal_primary_oai_HAL_hal_01141537v1 webofscience_primary_000356111100015CitationCount |
| ProviderPackageCode | CITATION AAYXX |
| PublicationCentury | 2000 |
| PublicationDate | 2015-06-24 |
| PublicationDateYYYYMMDD | 2015-06-24 |
| PublicationDate_xml | – month: 06 year: 2015 text: 2015-06-24 day: 24 |
| PublicationDecade | 2010 |
| PublicationPlace | OXFORD |
| PublicationPlace_xml | – name: OXFORD |
| PublicationTitle | Tetrahedron |
| PublicationTitleAbbrev | TETRAHEDRON |
| PublicationYear | 2015 |
| Publisher | Elsevier Ltd Elsevier |
| Publisher_xml | – name: Elsevier Ltd – name: Elsevier |
| References | Jayamurugan, Gisselbrecht, Boudon, Schoenebeck, Schweizer, Bernet, Diederich, Reisinger, Rivera-Fuentes, Lampart, Schweizer, Diederich, Shoji, Ito, Okujima, Morita, Jayamurugan, Finke, Gisselbrecht, Boudon, Schweizer, Diederich, Gawel, Dengiz, Finke, Trapp, Boudon, Gisselbrecht, Diederich (bib2) 2011; 17 was calculated for DMA moieties with the following formula Berkovitch-Yellin, Leiserowitz, Januszewski, Wendinger, Methfessel, Hampel, Tykwinski, Ueta, Hida, Nishiuchi, Kawamura (bib12) 1977; 33 0; for fully quinoid rings 0.10–0.12 Å. Kaiser, Hafner, Gajewski, Cavender (bib14) 1970; 9 Wu, Wu, Liu, Jen, Mochida, Yamazaki, Morioka, Yoshizawa, Nishida, Yamashita, Michinobu, May, Lim, Boudon, Gisselbrecht, Seiler, Gross, Biaggio, Diederich, Shoji, Ito, Toyota, Yasunami, Morita, Shoji, Higashi, Ito, Okujima, Yasunami, Morita, Koszelewski, Nowak-Król, Gryko, García, Herranz, Torres, Bouit, Delgado, Calbo, Viruela, Ortí, Martín, Betou, Kerisit, Meledje, Leroux, Katan, Halet, Guillemin, Trolez (bib1) 1998; 121 2]. For benzene Quinoid character + Finke, Haberland, Schweizer, Chen, Diederich, Finke, Diederich (bib4) 2013; 52 Andrew, Cox, Swager, Andrew, Bulovic (bib3) 2010; 12 Möllerstedt, Piqueras, Crespo, Ottosson, Ottosson, Kilså, Chajara, Piqueras, Crespo, Kato, Muthas, Dahlstrand, Yamazaki, Kilså, Ottosson, Endo, Hasegawa, Matsui, Yagi, Hino, Mazaki (bib7) 2004; 126 4 Jarowski, Wu, Boudon, Gisselbrecht, Gross, Schweizer, Diederich (bib15) 2009; 7 Bouvy, Janousek, Viehe, Tinant, Declercq, Bouvy, Janousek, Viehe, Wu, Tancini, Schweizer, Paunescu, Boudon, Gisselbrecht, Jarowski, Dalcanale, Diederich (bib11) 1993; 34 Jayamurugan, Dumele, Gisselbrecht, Boudon, Schweizer, Bernet, Diederich (bib6) 2013; 135 Elsevier, Kleijn, Ruitenberg, Vermeer, Elsevier, Kleijn, Boersma, Vermeer, Tsuji, Mandai (bib13) 1983; 5 Finke, Dumele, Zalibera, Confortin, Cias, Jayamurugan, Gisselbrecht, Boudon, Schweizer, Gescheidt, Diederich (bib5) 2012; 134 Gholami, Ramsaywack, Chaur, Murray, McDonald, Ferguson, Echegoyen, Tykwinski (bib8) 2013; 19 Toda, Shimazaki, Mukai, Iyoda, Tanake, Nishioka, Oda (bib9) 1987; 26 = Ueta (10.1016/j.tet.2015.03.081_bib12c) 2014; 12 Morioka (10.1016/j.tet.2015.03.081_bib1c) 2004; 33 Tinant (10.1016/j.tet.2015.03.081_bib11b) 1993 Januszewski (10.1016/j.tet.2015.03.081_bib12b) 2013; 52 Koszelewski (10.1016/j.tet.2015.03.081_bib1g) 2012; 7 Gawel (10.1016/j.tet.2015.03.081_bib2e) 2014; 53 Iyoda (10.1016/j.tet.2015.03.081_bib9b) 1983; 24 Michinobu (10.1016/j.tet.2015.03.081_bib1d) 2005 Andrew (10.1016/j.tet.2015.03.081_bib3b) 2012; 6 10.1016/j.tet.2015.03.081_bib10b Bouvy (10.1016/j.tet.2015.03.081_bib11a) 1993; 34 Reisinger (10.1016/j.tet.2015.03.081_bib2b) 2011; 17 Gholami (10.1016/j.tet.2015.03.081_bib8) 2013; 19 Finke (10.1016/j.tet.2015.03.081_bib5) 2012; 134 Jayamurugan (10.1016/j.tet.2015.03.081_bib2a) 2011 Jarowski (10.1016/j.tet.2015.03.081_bib15) 2009; 7 Dahlstrand (10.1016/j.tet.2015.03.081_bib7c) 2010; 75 Elsevier (10.1016/j.tet.2015.03.081_bib13b) 1986; 5 Endo (10.1016/j.tet.2015.03.081_bib7d) 2014; 16 Dehu (10.1016/j.tet.2015.03.081_bib10a) 1993; 115 Berkovitch-Yellin (10.1016/j.tet.2015.03.081_bib12a) 1977; 33 Finke (10.1016/j.tet.2015.03.081_bib4b) 2015; 15 Toda (10.1016/j.tet.2015.03.081_bib9a) 1987; 26 Wu (10.1016/j.tet.2015.03.081_bib11c) 2012; 7 Ottosson (10.1016/j.tet.2015.03.081_bib7b) 2007; 13 Wu (10.1016/j.tet.2015.03.081_bib1a) 1998; 121 Shoji (10.1016/j.tet.2015.03.081_bib2c) 2012; 10 Finke (10.1016/j.tet.2015.03.081_sref1) 2013; 52 Tsuji (10.1016/j.tet.2015.03.081_bib13c) 1995; 34 Betou (10.1016/j.tet.2015.03.081_bib1i) 2014; 20 Elsevier (10.1016/j.tet.2015.03.081_bib13a) 1983 Gajewski (10.1016/j.tet.2015.03.081_bib14b) 1971; 16 Shoji (10.1016/j.tet.2015.03.081_bib1f) 2011; 17 Jayamurugan (10.1016/j.tet.2015.03.081_bib2d) 2014; 79 Jayamurugan (10.1016/j.tet.2015.03.081_bib6) 2013; 135 Mochida (10.1016/j.tet.2015.03.081_bib1b) 2002 Shoji (10.1016/j.tet.2015.03.081_bib1e) 2008; 14 García (10.1016/j.tet.2015.03.081_bib1h) 2012; 77 Kaiser (10.1016/j.tet.2015.03.081_bib14a) 1970; 9 Möllerstedt (10.1016/j.tet.2015.03.081_bib7a) 2004; 126 Andrew (10.1016/j.tet.2015.03.081_bib3a) 2010; 12 Shoji, T (WOS:000310215100015) 2012; 10 Shoji, T (WOS:000290213100023) 2011; 17 DEHU, C (WOS:A1993LT17300039) 1993; 115 Andrew, TL (WOS:000284080400058) 2010; 12 KAISER, R (WOS:A1970I028500007) 1970; 9 Mollerstedt, H (WOS:000224873600031) 2004; 126 Wu, YL (WOS:000304440600006) 2012; 7 Januszewski, JA (WOS:000314650600041) 2013; 52 Tsuji, J (WOS:A1996TP36800001) 1995; 34 BOUVY, D (WOS:A1993KT35700023) 1993; 34 Michinobu, T (WOS:000226704300011) 2005 Endo, Y (WOS:000344635200026) 2014; 16 Finke, AD (WOS:000310483500045) 2012; 134 BERKOVITCHYELLIN, Z (WOS:A1977EF42800006) 1977; 33 Wu, XM (WOS:000079041700038) 1999; 121 Koszelewski, D (WOS:000306316300021) 2012; 7 Mochida, T (WOS:000177931900022) 2002 TODA, T (WOS:A1987H664200011) 1987; 26 Garcia, R (WOS:000311926100025) 2012; 77 Jarowski, PD (WOS:000264349200011) 2009; 7 Finke, AD (WOS:000350061300002) 2015; 15 Jayamurugan, G (WOS:000288866300058) 2011; 47 Gawel, P (WOS:000334396800010) 2014; 53 GAJEWSKI, JJ (WOS:A1971J080300002) 1971 ELSEVIER, CJ (WOS:A1983RV85000038) 1983 Reisinger, CM (WOS:000297737900014) 2011; 17 Gholami, M (WOS:000326290300013) 2013; 19 Ottosson, H (WOS:000249039700024) 2007; 13 TINANT, B (WOS:A1993LB78100016) 1993 Jayamurugan, G (WOS:000329472900040) 2014; 79 Jayamurugan, G (WOS:000315936700049) 2013; 135 Andrew, TL (WOS:000305661300014) 2012; 6 IYODA, M (WOS:A1983QX14000017) 1983; 24 ELSEVIER, CJ (WOS:A1986A913700015) 1986; 5 Morioka, Y (WOS:000223951900058) 2004; 33 Finke, AD (WOS:000323829600049) 2013; 52 Dahlstrand, C (WOS:000284519900008) 2010; 75 Shoji, T (WOS:000259913900036) 2008; 14 Betou, M (WOS:000340176600014) 2014; 20 Ueta, S (WOS:000334202900016) 2014; 12 |
| References_xml | – volume: 5 start-page: 1529 year: 1983 end-page: 1530 ident: bib13 publication-title: J. Chem. Soc., Chem. Commun. – volume: 12 start-page: 5302 year: 2010 end-page: 5305 ident: bib3 publication-title: Org. Lett. – volume: 52 start-page: 9827 year: 2013 end-page: 9830 ident: bib4 publication-title: Angew. Chem., Int. Ed. – reference: )/4]−[( – volume: 9 start-page: 892 year: 1970 end-page: 893 ident: bib14 publication-title: Angew. Chem., Int. Ed. Engl. – reference: =0.10–0.12 Å. – volume: 121 start-page: 472 year: 1998 end-page: 473 ident: bib1 publication-title: J. Am. Chem. Soc. – reference: + – reference: Quinoid character – volume: 135 start-page: 3599 year: 2013 end-page: 3606 ident: bib6 publication-title: J. Am. Chem. Soc. – reference: =[( – volume: 19 start-page: 15120 year: 2013 end-page: 15132 ident: bib8 publication-title: Chem.—Eur. J. – volume: 7 start-page: 1312 year: 2009 end-page: 1322 ident: bib15 publication-title: Org. Biomol. Chem. – volume: 33 start-page: 3657 year: 1977 end-page: 3669 ident: bib12 publication-title: Acta Crystallogr., Sect. B: Struct. Sci. – volume: 134 start-page: 18139 year: 2012 end-page: 18146 ident: bib5 publication-title: J. Am. Chem. Soc. – volume: 126 start-page: 13938 year: 2004 end-page: 13939 ident: bib7 publication-title: J. Am. Chem. Soc. – volume: 17 start-page: 4520 year: 2011 end-page: 4522 ident: bib2 publication-title: Chem. Commun. – reference: was calculated for DMA moieties with the following formula: – reference: )/2]. For benzene, – volume: 34 start-page: 1779 year: 1993 end-page: 1782 ident: bib11 publication-title: Tetrahedron Lett. – volume: 26 start-page: 335 year: 1987 end-page: 336 ident: bib9 publication-title: Angew. Chem., Int. Ed. Engl. – reference: =0; for fully quinoid rings, – volume: 115 start-page: 6198 year: 1993 ident: 10.1016/j.tet.2015.03.081_bib10a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja00067a039 – volume: 5 start-page: 716 year: 1986 ident: 10.1016/j.tet.2015.03.081_bib13b publication-title: Organometallics doi: 10.1021/om00135a015 – volume: 10 start-page: 8308 year: 2012 ident: 10.1016/j.tet.2015.03.081_bib2c publication-title: Org. Biomol. Chem. doi: 10.1039/c2ob26028j – volume: 79 start-page: 426 year: 2014 ident: 10.1016/j.tet.2015.03.081_bib2d publication-title: J. Org. Chem. doi: 10.1021/jo402440m – volume: 17 start-page: 5116 year: 2011 ident: 10.1016/j.tet.2015.03.081_bib1f publication-title: Chem.—Eur. J. doi: 10.1002/chem.201003628 – volume: 14 start-page: 8398 year: 2008 ident: 10.1016/j.tet.2015.03.081_bib1e publication-title: Chem.—Eur. J. doi: 10.1002/chem.200701981 – start-page: 4520 year: 2011 ident: 10.1016/j.tet.2015.03.081_bib2a publication-title: Chem. Commun. doi: 10.1039/c1cc10247h – volume: 52 start-page: 9827 year: 2013 ident: 10.1016/j.tet.2015.03.081_sref1 publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201304767 – volume: 7 start-page: 1185 year: 2012 ident: 10.1016/j.tet.2015.03.081_bib11c publication-title: Chem. Asian J. doi: 10.1002/asia.201100997 – start-page: 911 year: 1993 ident: 10.1016/j.tet.2015.03.081_bib11b publication-title: J. Chem. Soc., Perkin Trans. 2 doi: 10.1039/p29930000911 – volume: 9 start-page: 892 year: 1970 ident: 10.1016/j.tet.2015.03.081_bib14a publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/anie.197008922 – volume: 16 start-page: 1057 year: 1971 ident: 10.1016/j.tet.2015.03.081_bib14b publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(01)96624-9 – ident: 10.1016/j.tet.2015.03.081_bib10b – volume: 121 start-page: 472 year: 1998 ident: 10.1016/j.tet.2015.03.081_bib1a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja983537+ – volume: 16 start-page: 5608 year: 2014 ident: 10.1016/j.tet.2015.03.081_bib7d publication-title: Org. Lett. doi: 10.1021/ol502675n – start-page: 737 year: 2005 ident: 10.1016/j.tet.2015.03.081_bib1d publication-title: Chem. Commun. doi: 10.1039/B417393G – volume: 7 start-page: 1887 year: 2012 ident: 10.1016/j.tet.2015.03.081_bib1g publication-title: Chem. Asian J. doi: 10.1002/asia.201200179 – volume: 7 start-page: 1312 year: 2009 ident: 10.1016/j.tet.2015.03.081_bib15 publication-title: Org. Biomol. Chem. doi: 10.1039/b821230a – volume: 17 start-page: 12906 year: 2011 ident: 10.1016/j.tet.2015.03.081_bib2b publication-title: Chem.—Eur. J. doi: 10.1002/chem.201102852 – volume: 19 start-page: 15120 year: 2013 ident: 10.1016/j.tet.2015.03.081_bib8 publication-title: Chem.—Eur. J. doi: 10.1002/chem.201302452 – volume: 52 start-page: 1817 year: 2013 ident: 10.1016/j.tet.2015.03.081_bib12b publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201208058 – volume: 134 start-page: 18139 year: 2012 ident: 10.1016/j.tet.2015.03.081_bib5 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja309141r – volume: 126 start-page: 13938 year: 2004 ident: 10.1016/j.tet.2015.03.081_bib7a publication-title: J. Am. Chem. Soc. doi: 10.1021/ja045729c – volume: 33 start-page: 1190 year: 2004 ident: 10.1016/j.tet.2015.03.081_bib1c publication-title: Chem. Lett. doi: 10.1246/cl.2004.1190 – volume: 12 start-page: 2784 year: 2014 ident: 10.1016/j.tet.2015.03.081_bib12c publication-title: Org. Biomol. Chem. doi: 10.1039/c3ob42574f – volume: 77 start-page: 10707 year: 2012 ident: 10.1016/j.tet.2015.03.081_bib1h publication-title: J. Org. Chem. doi: 10.1021/jo302047m – volume: 26 start-page: 335 year: 1987 ident: 10.1016/j.tet.2015.03.081_bib9a publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/anie.198703351 – volume: 12 start-page: 5302 year: 2010 ident: 10.1016/j.tet.2015.03.081_bib3a publication-title: Org. Lett. doi: 10.1021/ol102384k – start-page: 3559 year: 2002 ident: 10.1016/j.tet.2015.03.081_bib1b publication-title: J. Chem. Soc., Dalton Trans. doi: 10.1039/b204168e – volume: 13 start-page: 6998 year: 2007 ident: 10.1016/j.tet.2015.03.081_bib7b publication-title: Chem.—Eur. J. doi: 10.1002/chem.200700362 – start-page: 1529 year: 1983 ident: 10.1016/j.tet.2015.03.081_bib13a publication-title: J. Chem. Soc., Chem. Commun. doi: 10.1039/c39830001529 – volume: 20 start-page: 9553 year: 2014 ident: 10.1016/j.tet.2015.03.081_bib1i publication-title: Chem.—Eur. J. doi: 10.1002/chem.201402653 – volume: 53 start-page: 4341 year: 2014 ident: 10.1016/j.tet.2015.03.081_bib2e publication-title: Angew. Chem., Int. Ed. doi: 10.1002/anie.201402299 – volume: 34 start-page: 2589 year: 1995 ident: 10.1016/j.tet.2015.03.081_bib13c publication-title: Angew. Chem., Int. Ed. Engl. doi: 10.1002/anie.199525891 – volume: 24 start-page: 2861 year: 1983 ident: 10.1016/j.tet.2015.03.081_bib9b publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)88044-2 – volume: 6 start-page: 4671 year: 2012 ident: 10.1016/j.tet.2015.03.081_bib3b publication-title: ACS Nano doi: 10.1021/nn301851k – volume: 15 start-page: 19 year: 2015 ident: 10.1016/j.tet.2015.03.081_bib4b publication-title: Chem. Rec. doi: 10.1002/tcr.201402060 – volume: 34 start-page: 1779 year: 1993 ident: 10.1016/j.tet.2015.03.081_bib11a publication-title: Tetrahedron Lett. doi: 10.1016/S0040-4039(00)60777-3 – volume: 75 start-page: 8060 year: 2010 ident: 10.1016/j.tet.2015.03.081_bib7c publication-title: J. Org. Chem. doi: 10.1021/jo101634v – volume: 33 start-page: 3657 year: 1977 ident: 10.1016/j.tet.2015.03.081_bib12a publication-title: Acta Crystallogr., Sect. B: Struct. Sci. doi: 10.1107/S0567740877011819 – volume: 135 start-page: 3599 year: 2013 ident: 10.1016/j.tet.2015.03.081_bib6 publication-title: J. Am. Chem. Soc. doi: 10.1021/ja312084s – volume: 15 start-page: 19 year: 2015 ident: WOS:000350061300002 article-title: 6,6-Dicyanopentafulvenes: Teaching an Old Dog New Tricks publication-title: CHEMICAL RECORD doi: 10.1002/tcr.201402060 – start-page: 3559 year: 2002 ident: WOS:000177931900022 article-title: Mono- and diferrocenyl complexes with electron-accepting moieties formed by the reaction of ferrocenylalkynes with tetra-cyanoethylene publication-title: JOURNAL OF THE CHEMICAL SOCIETY-DALTON TRANSACTIONS doi: 10.1039/b204168e – volume: 5 start-page: 716 year: 1986 ident: WOS:A1986A913700015 article-title: SYNTHESIS, STRUCTURE, AND REACTIVITY OF SOME (OMICRON-ALLENYL)PALLADIUM(II) AND (OMICRON-PROP-2-YNYL)PALLADIUM(II) COMPLEXES publication-title: ORGANOMETALLICS – volume: 53 start-page: 4341 year: 2014 ident: WOS:000334396800010 article-title: Synthesis of Cyano-Substituted Diaryltetracenes from Tetraaryl[3] cumulenes** publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201402299 – volume: 126 start-page: 13938 year: 2004 ident: WOS:000224873600031 article-title: Fulvenes, fulvalenes, and azulene: Are they aromatic chameleons? publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja045729c – volume: 10 start-page: 8308 year: 2012 ident: WOS:000310215100015 article-title: Synthesis of push-pull chromophores by the sequential [2+2] cycloaddition of 1-azulenylbutadiynes with tetracyanoethylene and tetrathiafulvalene publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c2ob26028j – volume: 20 start-page: 9553 year: 2014 ident: WOS:000340176600014 article-title: High-Yield Formation of Substituted Tetracyanobutadienes from Reaction of Ynamides with Tetracyanoethylene publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201402653 – volume: 16 start-page: 5608 year: 2014 ident: WOS:000344635200026 article-title: Synthesis and Electronic Structure of Dicyanofulvene-Fused Electron Accepting Molecule Based on a 1,5-Dihydro-s-Indacene Framework publication-title: ORGANIC LETTERS doi: 10.1021/ol502675n – volume: 34 start-page: 2589 year: 1995 ident: WOS:A1996TP36800001 article-title: Palladium-catalyzed reactions of propargylic compounds in organic synthesis publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 75 start-page: 8060 year: 2010 ident: WOS:000284519900008 article-title: Substituent Effects on the Electron Affinities and Ionization Energies of Tria-, Penta-, and Heptafulvenes: A Computational Investigation publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo101634v – volume: 9 start-page: 892 year: 1970 ident: WOS:A1970I028500007 article-title: SIMPLE SYNTHESIS OF 1,2-DIHYDROPENTALENE AND ITS SUBSTITUTION PRODUCTS publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION – volume: 7 start-page: 1185 year: 2012 ident: WOS:000304440600006 article-title: Proacetylenic Reactivity of a Push-Pull Buta-1,2,3-triene: New Chromophores and Supramolecular Systems publication-title: CHEMISTRY-AN ASIAN JOURNAL doi: 10.1002/asia.201100997 – volume: 14 start-page: 8398 year: 2008 ident: WOS:000259913900036 article-title: Synthesis, Properties, and Redox Behavior of Mono-, Bis-, and Tris[1,1,4,4,-tetracyano-2-(1-azulenyl)-3-butadienyl] Chromophores Binding with Benzene and Thiophene Cores publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200701981 – volume: 121 start-page: 472 year: 1999 ident: WOS:000079041700038 article-title: Highly efficient, thermally and chemically stable second order nonlinear optical chromophores containing a 2-phenyl-tetracyanobutadienyl acceptor publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 12 start-page: 2784 year: 2014 ident: WOS:000334202900016 article-title: Regioisomeric allene dimer formation by the reaction of tetraarylbutatrienes with tetracyanoethene publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/c3ob42574f – volume: 24 start-page: 2861 year: 1983 ident: WOS:A1983QX14000017 article-title: SYNTHESIS AND PROPERTIES OF BUTATRIENES CONTAINING A BISDEHYDRO[13]ANNULENE SYSTEM AS TERMINAL GROUPS publication-title: TETRAHEDRON LETTERS – volume: 135 start-page: 3599 year: 2013 ident: WOS:000315936700049 article-title: Expanding the Chemical Structure Space of Opto-Electronic Molecular Materials: Unprecedented Push-Pull Chromophores by Reaction of a Donor-Substituted Tetracyanofulvene with Electron-Rich Alkynes publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja312084s – volume: 52 start-page: 9827 year: 2013 ident: WOS:000323829600049 article-title: A Mild, Thermal Pentafulvene-to-Benzene Rearrangement publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201304767 – volume: 115 start-page: 6198 year: 1993 ident: WOS:A1993LT17300039 article-title: DONOR-ACCEPTOR DIPHENYLACETYLENES - GEOMETRIC STRUCTURE, ELECTRONIC-STRUCTURE, AND 2ND-ORDER NONLINEAR-OPTICAL PROPERTIES publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY – volume: 7 start-page: 1312 year: 2009 ident: WOS:000264349200011 article-title: New donor-acceptor chromophores by formal [2+2] cycloaddition of donor-substituted alkynes to dicyanovinyl derivatives publication-title: ORGANIC & BIOMOLECULAR CHEMISTRY doi: 10.1039/b821230a – start-page: 1529 year: 1983 ident: WOS:A1983RV85000038 article-title: ALLENYLPALLADIUM(II) SPECIES - POSSIBLE INTERMEDIATES IN THE TETRAKIS(TRIPHENYLPHOSPHINE)PALLADIUM(0)-CATALYSED FORMATION OF ALLENES FROM PROP-2-YNYLIC SUBSTRATES publication-title: JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS – start-page: 737 year: 2005 ident: WOS:000226704300011 article-title: A new class of organic donor-acceptor molecules with large third-order optical nonlinearities publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/b417393g – volume: 47 start-page: 4520 year: 2011 ident: WOS:000288866300058 article-title: Expanding the chemical space for push-pull chromophores by non-concerted [2+2] and [4+2] cycloadditions: access to a highly functionalised 6,6-dicyanopentafulvene with an intense, low-energy charge-transfer band publication-title: CHEMICAL COMMUNICATIONS doi: 10.1039/c1cc10247h – volume: 7 start-page: 1887 year: 2012 ident: WOS:000306316300021 article-title: Selective Cycloaddition of Tetracyanoethene (TCNE) and 7,7,8,8-Tetracyano-p-quinodimethane (TCNQ) to Afford meso-Substituted Phenylethynyl Porphyrins publication-title: CHEMISTRY-AN ASIAN JOURNAL doi: 10.1002/asia.201200179 – volume: 34 start-page: 1779 year: 1993 ident: WOS:A1993KT35700023 article-title: CUMULOGY SUPPORTED BY X-RAY-ANALYSIS OF 1,1-BIS(DIMETHYLAMINO)-4,4-DICYANOBUTATRIENE publication-title: TETRAHEDRON LETTERS – volume: 26 start-page: 335 year: 1987 ident: WOS:A1987H664200011 article-title: SYNTHESIS AND PROPERTIES OF 1-CYCLOHEPTATRIENYLIDENE-2-CYCLOPENTADIENYLIDENEETHYLENE DERIVATIVES publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH – start-page: 911 year: 1993 ident: WOS:A1993LB78100016 article-title: EXCEPTIONALLY SHORT CENTRAL BONDS IN THE CUMULOGUE AND THE VINYLOGUE OF 2,2-DICYANO-1,1-BIS(DIMETHYLAMINO)ETHYLENE publication-title: JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 – volume: 12 start-page: 5302 year: 2010 ident: WOS:000284080400058 article-title: Synthesis, Reactivity, and Electronic Properties of 6,6-Dicyanofulvenes publication-title: ORGANIC LETTERS doi: 10.1021/ol102384k – volume: 13 start-page: 6998 year: 2007 ident: WOS:000249039700024 article-title: Scope and limitations of Baird's theory on triplet state aromaticity: Application to the tuning of singlet-triplet energy gaps in fulvenes publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.200700362 – volume: 17 start-page: 5116 year: 2011 ident: WOS:000290213100023 article-title: Synthesis of Redox-Active, Intramolecular Charge-Transfer Chromophores by the [2+2] Cycloaddition of Ethynylated 2H-Cyclohepta[b]furan-2-ones with Tetracyanoethylene publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201003628 – volume: 17 start-page: 12906 year: 2011 ident: WOS:000297737900014 article-title: Cascade Pericyclic Reactions of Alleno-Acetylenes: Facile Access to Highly Substituted Cyclobutene, Dendralene, Pentalene, and Indene Skeletons publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201102852 – volume: 33 start-page: 1190 year: 2004 ident: WOS:000223951900058 article-title: Novel donor-pi-acceptor compounds containing 1,3-dithiol-2-ylidene and tetracyanobutadiene units publication-title: CHEMISTRY LETTERS doi: 10.1246/cl.2004.1190 – volume: 52 start-page: 1817 year: 2013 ident: WOS:000314650600041 article-title: Synthesis and Structure of Tetraarylcumulenes: Characterization of Bond-Length Alternation versus Molecule Length publication-title: ANGEWANDTE CHEMIE-INTERNATIONAL EDITION doi: 10.1002/anie.201208058 – volume: 19 start-page: 15120 year: 2013 ident: WOS:000326290300013 article-title: Synthesis and Derivatization of Expanded [n]Radialenes (n=3, 4) publication-title: CHEMISTRY-A EUROPEAN JOURNAL doi: 10.1002/chem.201302452 – start-page: 1057 year: 1971 ident: WOS:A1971J080300002 article-title: FACILE THERMAL CYCLIZATION OF 6-VINYLFULVENE TO DIHYDROPENTALENE publication-title: TETRAHEDRON LETTERS – volume: 33 start-page: 3657 year: 1977 ident: WOS:A1977EF42800006 article-title: ELECTRON-DENSITY DISTRIBUTION IN CUMULENES - X-RAY STUDY OF TETRAPHENYLBUTATRIENE AT 20-DEGREES-C AND -160-DEGREES-C publication-title: ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE – volume: 77 start-page: 10707 year: 2012 ident: WOS:000311926100025 article-title: Tuning the Electronic Properties of Nonplanar exTTF-Based Push-Pull Chromophores by Aryl Substitution publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo302047m – volume: 6 start-page: 4671 year: 2012 ident: WOS:000305661300014 article-title: Bulk Heterojuction Solar Cells Containing 6,6-Dicyanofulvenes as n-Type Additives publication-title: ACS NANO doi: 10.1021/nn301851k – volume: 134 start-page: 18139 year: 2012 ident: WOS:000310483500045 article-title: 6,6-Dicyanopentafulvenes: Electronic Structure and Regioselectivity in [2+2] Cycloaddition-Retroelectrocyclization Reactions publication-title: JOURNAL OF THE AMERICAN CHEMICAL SOCIETY doi: 10.1021/ja309141r – volume: 79 start-page: 426 year: 2014 ident: WOS:000329472900040 article-title: One-Pot Access to Push-Pull Oligoenes by Sequential [2+2] Cycloaddition-Retroelectrocyclization Reactions publication-title: JOURNAL OF ORGANIC CHEMISTRY doi: 10.1021/jo402440m |
| SSID | ssj0001123 |
| Score | 2.227758 |
| Snippet | We report the preparation of a 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene from a 6,6-dibromopentafulvene and 4-ethynyl-N,N-dimethylaniline under... We report the preparation of a 6,6-bis[(4-N,N-dimethylanilino)ethynyl]pentafulvene from a 6,6-dibromopentafulvene and 4-ethynyl-NN-dimethylaniline under... |
| Source | Web of Science |
| SourceID | hal proquest webofscience crossref elsevier |
| SourceType | Open Access Repository Aggregation Database Enrichment Source Index Database Publisher |
| StartPage | 4393 |
| SubjectTerms | [2+2] Cycloaddition chemical reactions Chemical Sciences chemical structure Chemistry Chemistry, Organic Cumulene dihydropentalene Electrocyclization Organic chemistry organic compounds Pentafulvenes Physical Sciences Science & Technology spectroscopy X-radiation |
| Title | New reactivity of 6,6-bis-donor-substituted pentafulvenes: one-step synthesis of highly substituted [3]cumulene and dihydropentalene |
| URI | https://dx.doi.org/10.1016/j.tet.2015.03.081 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000356111100015 https://www.proquest.com/docview/2000271662 https://univ-rennes.hal.science/hal-01141537 |
| Volume | 71 |
| WOS | 000356111100015 |
| WOSCitedRecordID | wos000356111100015 |
| hasFullText | 1 |
| inHoldings | 1 |
| isFullTextHit | |
| isPrint | |
| journalDatabaseRights | – providerCode: PRVESC databaseName: Baden-Württemberg Complete Freedom Collection (Elsevier) customDbUrl: eissn: 1464-5416 dateEnd: 99991231 omitProxy: true ssIdentifier: ssj0001123 issn: 0040-4020 databaseCode: GBLVA dateStart: 20110101 isFulltext: true titleUrlDefault: https://www.sciencedirect.com providerName: Elsevier – providerCode: PRVESC databaseName: Elsevier SD Freedom Collection customDbUrl: eissn: 1464-5416 dateEnd: 99991231 omitProxy: true ssIdentifier: ssj0001123 issn: 0040-4020 databaseCode: .~1 dateStart: 19950101 isFulltext: true titleUrlDefault: https://www.sciencedirect.com providerName: Elsevier – providerCode: PRVESC databaseName: Elsevier SD Freedom Collection customDbUrl: eissn: 1464-5416 dateEnd: 99991231 omitProxy: true ssIdentifier: ssj0001123 issn: 0040-4020 databaseCode: ACRLP dateStart: 19950102 isFulltext: true titleUrlDefault: https://www.sciencedirect.com providerName: Elsevier – providerCode: PRVESC databaseName: Elsevier SD Freedom Collection Journals [SCFCJ] customDbUrl: eissn: 1464-5416 dateEnd: 99991231 omitProxy: true ssIdentifier: ssj0001123 issn: 0040-4020 databaseCode: AIKHN dateStart: 19950102 isFulltext: true titleUrlDefault: https://www.sciencedirect.com providerName: Elsevier – providerCode: PRVLSH databaseName: Elsevier Journals customDbUrl: mediaType: online eissn: 1464-5416 dateEnd: 99991231 omitProxy: true ssIdentifier: ssj0001123 issn: 0040-4020 databaseCode: AKRWK dateStart: 19930101 isFulltext: true providerName: Library Specific Holdings |
| link | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1Lb9QwELZKe4BLVV5iS6kM6qnCNIkdJ8tttaJaCuqJSpUqZPkxUReVZNVkkfbCiR_OTB7LIkGFOEWx7CjrceabWX_-hrGjkKUBtAOByY8XKrdWYBoRRKxBWY2YPy5atc9zPbtQZ5fp5RabDmdhiFbZ-_7Op7feum856WfzZDGf0xlfFVH2gyENXlOS3Sb1L1zTb77_onlgPLFmzlHvYWez5Xg1QHTKOG11TvP4b9h075pIkhsR6B8wqsWj0z222weSfNK960O2BeUjdn861G97zH6g_-IYEvquPgSvCq5fa8yEaxGqsroVNfqMjigQ-IIo5AXRpNH1veVVCQLNv-D1qsQIsZ7XNJykjW9WfHPclfzsl1-XCF3AbRl4mF-vAv2_T4cssfEJuzh992k6E33NBeFTJRvhnc5tDi7YuIh0AojvGcYMaZ54_JLHOJnBQY7GSbPCJeDVOHYQFZj2OFdkAeRTtl3iSz5jXOoiddbHweZOeQtOOyelBC8BMDV2IxYNs218L0hOdTFuzMA8-2LQQIYMZCJp0EAjdrwesujUOO7qrAYTmt-WlEG0uGvYKzT3-vEkvz2bfDTURskjIkT2DTu9HFaDQbPSJostoVrWVNYTM_1Y62TEjjaXyfqJ7e6tJqhqD7KPWPwv3ab9DJFUQbP_fz_tOXtAd8R0S9QB225ul_ACY6rGHbYfzSHbmbz_MDv_CVuMIlQ |
| linkProvider | Elsevier |
| linkToHtml | http://utb.summon.serialssolutions.com/2.0.0/link/0/eLvHCXMwnV1La9wwEBbJ5pBeSp90-1RLTqUia1uWvb0tS4PTbPeUQKAUoceYbEjtJfYW9t4f3hm_2EIbSk8GWWNsjTTfjPVphrEjn8QelAWBwY8TMjVGYBjhRaBAGoWYP82bbJ9LlV3Iz5fx5R6b92dhiFbZ2f7WpjfWums57kbzeL1a0RlfOaHoB10avMZqnx3IGG3yiB3MTs-y5WCQ0aUYyHMk0G9uNjSvGohRGcRNqtM0-Bs87V8RT3LHCf0DTDWQdPKA3e98ST5rX_ch24PiETuc9yXcHrOfaMI4eoWuLRHBy5yrDwqD4Ur4sihvRYVmo-UKeL4mFnlOTGm0fh95WYDAGbDm1bZAJ7FaVSRO2Y1vtnxX7mv0zW2-bxC9gJvCc7-62nr6xU_nLLHxCbs4-XQ-z0RXdkG4WEa1cFalJgXrTZBPVAgI8Qm6DXEaOlzMUxxMbyFF_cRJbkNwchpYmOQY-VibJx6ip2xU4Es-YzxSeWyNC7xJrXQGrLI2iiJwEQBGx3bMJv1oa9flJKfSGDe6J59da1SQJgXpSaRRQWP2fhBZtwk57uosexXq32aVRsC4S-wdqnt4PGXgzmYLTW0UPyJIJD-w09t-NmhUK-2zmALKTUWVPTHYD5QKx-xod5oMT2w2cBWhVXOWfcyCf-k270aIshXUz__v096ww-z8y0IvTpdnL9g9ukPEt1C-ZKP6dgOv0MWq7etuCf0CIWgk_w |
| openUrl | ctx_ver=Z39.88-2004&ctx_enc=info%3Aofi%2Fenc%3AUTF-8&rfr_id=info%3Asid%2Fsummon.serialssolutions.com&rft_val_fmt=info%3Aofi%2Ffmt%3Akev%3Amtx%3Ajournal&rft.genre=article&rft.atitle=New+reactivity+of+6%2C6-bis-donor-substituted+pentafulvenes%3A+one-step+synthesis+of+highly+substituted+%5B3%5Dcumulene+and+dihydropentalene&rft.jtitle=Tetrahedron&rft.au=Kerisit%2C+Nicolas&rft.au=Finke%2C+Aaron+D.&rft.au=Trapp%2C+Nils&rft.au=Leroux%2C+Yann+R.&rft.date=2015-06-24&rft.pub=Elsevier&rft.issn=0040-4020&rft.volume=71&rft.issue=25&rft.spage=4393&rft.epage=4399&rft_id=info:doi/10.1016%2Fj.tet.2015.03.081&rft.externalDBID=n%2Fa&rft.externalDocID=000356111100015 |
| thumbnail_l | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/lc.gif&issn=0040-4020&client=summon |
| thumbnail_m | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/mc.gif&issn=0040-4020&client=summon |
| thumbnail_s | http://covers-cdn.summon.serialssolutions.com/index.aspx?isbn=/sc.gif&issn=0040-4020&client=summon |