title: Mechanistic aspects of alkyne migration in alkylidene carbenoid rearrangements.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Alberta, Edmonton, Alberta, T6G 2G2 Canada.
authors.forename: Paul
authors.initials: P
authors.lastname: Bichler
authors.forename: Wesley A
authors.initials: WA
authors.lastname: Chalifoux
authors.forename: Sara
authors.initials: S
authors.lastname: Eisler
authors.forename: Annabelle L K
authors.initials: AL
authors.lastname: Shi Shun
authors.forename: Erin T
authors.initials: ET
authors.lastname: Chernick
authors.forename: Rik R
authors.initials: RR
authors.lastname: Tykwinski