Generation and interception of bicyclo[3.2.1]oct-2-yne: an experimental and theoretical mechanistic study

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.