TY - JOUR
T1 - New Methods for the Synthesis of Vinyl Azides
AU - L'abbé, Gerrit
AU - Hassner, Alfred
PY - 1971/2
Y1 - 1971/2
N2 - 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.
AB - 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.
KW - Azides
KW - Synthetic methods
KW - Vinyl azides
UR - http://www.scopus.com/inward/record.url?scp=84979024369&partnerID=8YFLogxK
U2 - 10.1002/anie.197100981
DO - 10.1002/anie.197100981
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AN - SCOPUS:84979024369
SN - 0570-0833
VL - 10
SP - 98
EP - 104
JO - Angewandte Chemie - International Edition
JF - Angewandte Chemie - International Edition
IS - 2
ER -