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Updated: Jun 9, 2025

Metal-free Synthesis of Ynones from Acyl Chlorides and Potassium Alkynyltrifluoroborate Salts
Published on: February 24, 2015
Generation and interception of bicyclo[3.2.1]oct-2-yne: an experimental and theoretical mechanistic study
T E Anderson1, Beauty K Chabuka2, Igor V Alabugin2
1Department of Chemistry, Colby College, Waterville, Maine 04901, USA. dmthamat@colby.edu.
Abstract:
Bicyclo[3.2.1]oct-2-yne was generated from the Fritsch-Buttenberg-Wiechell rearrangement of 2-norbornylidene carbene. The rearrangement preferentially involves migration of a tertiary carbon over a secondary carbon, a trend that contrasts with rearrangements of acyclic carbenes and which may be attributable to hyperconjugative effects promoted by the bridged structure of the carbene.
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