Decoupling Deprotonation from Metalation: Thia-Fries Rearrangement
Aufgeklärt: Mithilfe von 2H‐, 18O‐ und 34S‐markierten Aryltriflaten ließ sich zeigen, dass die Lithiumdiisopropylamid‐vermittelte Thia‐Fries‐Umlagerung über eine irreversible ortho‐Deprotonierung verläuft (siehe Schema; DIPA=Diisopropylamin, LDA=Lithiumdiisopropylamid). Die ortho‐Metallierung dagege...
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| Published in | Angewandte Chemie Vol. 120; no. 27; pp. 5145 - 5148 |
|---|---|
| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
WILEY-VCH Verlag
23.06.2008
WILEY‐VCH Verlag |
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| Online Access | Get full text |
| ISSN | 0044-8249 1521-3757 |
| DOI | 10.1002/ange.200800750 |
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| Abstract | Aufgeklärt: Mithilfe von 2H‐, 18O‐ und 34S‐markierten Aryltriflaten ließ sich zeigen, dass die Lithiumdiisopropylamid‐vermittelte Thia‐Fries‐Umlagerung über eine irreversible ortho‐Deprotonierung verläuft (siehe Schema; DIPA=Diisopropylamin, LDA=Lithiumdiisopropylamid). Die ortho‐Metallierung dagegen führt ausschließlich zur Bildung eines Benz‐ins. |
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| AbstractList | Aufgeklärt: Mithilfe von 2H‐, 18O‐ und 34S‐markierten Aryltriflaten ließ sich zeigen, dass die Lithiumdiisopropylamid‐vermittelte Thia‐Fries‐Umlagerung über eine irreversible ortho‐Deprotonierung verläuft (siehe Schema; DIPA=Diisopropylamin, LDA=Lithiumdiisopropylamid). Die ortho‐Metallierung dagegen führt ausschließlich zur Bildung eines Benz‐ins. |
| Author | Gill, Duncan M. Dyke, Alan M. Hester, Alison J. Harvey, Jeremy N. Lloyd-Jones, Guy C. Shepperson, Ian R. Muñoz, M. Paz |
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| References_xml | – reference: R. Huisgen, J. Sauer, Chem. Ber. Recueil 1959, 92, 192-202. The mechanism shown below was suggested for catalysis by R2NH: – reference: F. Scardiglia, J. D. Roberts, J. Org. Chem. 1958, 23, 629-631; – reference: T. Harada, M. Chiba, A. Oku, J. Org. Chem. 1999, 64, 8210-8213; – reference: Angew. Chem. Int. Ed. 2003, 42, 502-528; – reference: J. D. Roberts, C. W. Vaughan, L. A. Carlsmith, D. A. Semenow, J. Am. Chem. Soc. 1956, 78, 611-614; – reference: M. Panar, J. D. Roberts, J. Am. Chem. Soc. 1960, 82, 3629-3632. – reference: T. Kamikawa, T. Hayashi, Tetrahedron Lett. 1997, 38, 7087-7090; – reference: H. Sharghi, Z. Shahsavari-Fard, Helv. Chim. Acta 2005, 88, 42-52; – reference: Account: Y. Kondo, M. Ueno, Y. Tanaka, J. Synth. Org. Chem. Jpn. 2005, 63, 453-463. – reference: I. Sapountzis, W. Lin, M. Fischer, P. Knochel, Angew. Chem. 2004, 116, 4464-4466; – reference: H. Nozaki, R. Okada, R. Noyori, M. 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| Snippet | Aufgeklärt: Mithilfe von 2H‐, 18O‐ und 34S‐markierten Aryltriflaten ließ sich zeigen, dass die Lithiumdiisopropylamid‐vermittelte Thia‐Fries‐Umlagerung über... |
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| Title | Decoupling Deprotonation from Metalation: Thia-Fries Rearrangement |
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