Mechanistic aspects of alkyne migration in alkylidene carbenoid rearrangements.
The mechanism of the Fritsch-Buttenberg-Wiechell rearrangement of (13)C labeled precursors has been examined to determine the propensity of the alkynyl (R-CC-) group to migrate in an alkylidene carbenoid species. Reaction of dibromoolefins with n-BuLi and ketones with Me(3)SiC(Li)N(2) both demonstrate that the alkynyl moiety readily undergoes 1,2-migration from carbenoid intermediates.
Bichler
Paul
P
Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada.
Chalifoux
Wesley A
WA
Eisler
Sara
S
Shi Shun
Annabelle L K
AL
Chernick
Erin T
ET
Tykwinski
Rik R
RR