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1,4‐Didehydrobutadiene: The Intermediate in a New Class of Thermally Induced Intramolecular Alkyne Couplings
Author(s) -
Gleiter Rolf,
Ritter Joachim
Publication year - 1995
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199424701
Subject(s) - alkyne , intramolecular force , reactivity (psychology) , chemistry , thermal decomposition , photochemistry , solvent , trapping , stereochemistry , catalysis , organic chemistry , medicine , ecology , alternative medicine , pathology , biology
Nonconjugated diynes can also form diradicals by cyclization. Thermolysis of 1 (R = i Pr) initially yields 1,4‐didehydrobutadiene 2 , which reacts with a hydrogen donor R'H (e.g. solvent) to give the trapping products 3 and 4 . The reactivity of 1 is explained by the electronic activation of the alkyne units by the N atoms, a sufficiently small separation of the C atoms to be linked, and a gain in energy upon formation of the σ and π bonds.
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