Synthesis, Chemistry, and Photochemistry of Methylcyanobutadiyne in the Context of Space Science

An alternative preparation of methylcyanobutadiyne (MeC5N), a molecule present in the interstellar medium, was established in order to circumvent tedious steps from previous methods. The possibility of forming methylcyanoacetylene and MeC5N by gas-phase photolysis was evaluated from relevant acetyle...

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Published inJournal of organic chemistry Vol. 81; no. 9; pp. 3560 - 3567
Main Authors Kerisit, Nicolas, Rouxel, Cédric, Colombel-Rouen, Sophie, Toupet, Loïc, Guillemin, Jean-Claude, Trolez, Yann
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 06.05.2016
Amer Chemical Soc
Subjects
acetylene
Chemical Sciences
chemical structure
Chemistry
Chemistry, Organic
gases
Lewis bases
organic chemistry
photolysis
Physical Sciences
regioselectivity
Science & Technology
solvents
CN(X SIGMA(+))
SPECTROSCOPY
CROSSED-BEAM
CYANOACETYLENE
ALLENE
INTERSTELLAR-MEDIUM
CYANOVINYL PHOSPHATE
SPECTRA
CH3CCH XA
RADICAL SELF-REACTION
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ISSN0022-3263
1520-6904
1520-6904
DOI10.1021/acs.joc.6b00205

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Summary:An alternative preparation of methylcyanobutadiyne (MeC5N), a molecule present in the interstellar medium, was established in order to circumvent tedious steps from previous methods. The possibility of forming methylcyanoacetylene and MeC5N by gas-phase photolysis was evaluated from relevant acetylene derivatives in the context of space science. The reactivity of MeC5N toward simple nucleophiles was investigated. The exclusive formation of E adducts was observed, together with a solvent dependence for the regioselectivity of the addition.
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ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.6b00205