Base catalysed rearrangements involving ylide intermediates. Part 1. The rearrangements of diallyl- and allylpropynyl-ammonium cations

Abstract

The base catalysed rearrangements of diallylammonium rations and allylpropynylammonium rations are described. In most cases, the major product arises by a symmetry-allowed [3,2] sigmatropic rearrangement of the intermediate ylide. The minor products can be regarded as being derived by homolysis of the ylide into a radical pair followed by recombination.