Stevens-Type Rearrangement of Open-Chain Analogues of Reissert Compounds. Evidence for Participation by Radical Intermediates

Article abstract of DOI:10.1021/jo00321a026

The thermal rearrangements of the conjugate bases (2) of N-benzyl open-chain analogues of Reissert compounds give products formally derived from two competing <1,2> rearrangement-elimination reactions.The products of the major sequences of reactions are deoxybenzoins and benzonitriles, while those of the minor sequence are α-benzoamidostilbenes.The results are compatible with radical pair mechanism involving initial homolysis of the conjugate base 2 followed by two possible modes of radical recombination (Schemes I and II).