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New Methods for the Synthesis of Vinyl Azides
Author(s) -
L'abbé Gerrit,
Hassner Alfred
Publication year - 1971
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.197100981
Subject(s) - chemistry , dehydrohalogenation , azide , nucleophile , stereospecificity , halide , double bond , combinatorial chemistry , organic chemistry , polymer chemistry , catalysis
A critical survey of synthetic approaches to vinyl azides is presented, focusing especially on stereo‐ and regiochemical problems. The com bined procedure of azidohalogenation of olefins followed by dehydrohalogenation, leads to regiospecific and, in the case of ionic additions, also to stereospecific formation of vinyl azides. Nucleophilic substitutions by azide ions on activated olefinic halides result in β‐azidovinyl ketones, esters, nitriles, etc., and proceed predominantly with retention of configuration about the CC bond. The known synthetic methods leading to α‐azidovinyl ketones and esters give rise to the thermodynamically more stable trans‐vinyl azides.