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High‐Yield Formation of Substituted Tetracyanobutadienes from Reaction of Ynamides with Tetracyanoethylene
Author(s) -
Betou Marie,
Kerisit Nicolas,
Meledje Esme,
Leroux Yann R.,
Katan Claudine,
Halet JeanFrançois,
Guillemin JeanClaude,
Trolez Yann
Publication year - 2014
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201402653
Subject(s) - tetracyanoethylene , yield (engineering) , cycloaddition , chemistry , computational chemistry , photochemistry , organic chemistry , physics , catalysis , thermodynamics
A high‐yielding sequence of [2+2] cycloaddition–retroelectrocyclization of ynamides with tetracyanoethylene (TCNE) is described. The reaction provided tetracyanobutadiene (TCBD) species, which were characterized by various techniques. DFT and TD‐DFT calculations were also performed to complement experimental findings.