Thermal rearrangement of a 2-benzylidenecyclobutanone: a suprafacial [1,3]shift with inversion
Abstract
The optically active 2-E-benzylidene-4-t-butyl 4-cyano-3-phenylcyclobutanone (1) rearranges thermally to the 2-Z-benzylidene isomer (3) by a [1,3]sigmatropic shift with inversion of the migrating centre; a further thermal isomerisation of (3) is also described.