The preparation and rearrangement of some 2,3-oxygenated 2-phenylbornanes

Abstract

Reaction of the r-2-hydroxy-2-phenyl-c-3-p-tolylsulphonyloxybornanes (4b) and (10b) with base gave the epimeric 2,3-epoxy-2-phenylbornanes (1) and (2). Acid-catalysed rearrangement of the endo-epoxide (2) gave 2-endo-phenylbornan-3-one (8); similar reaction of the exo-epoxide (1) afforded the unsaturated aldehyde (6) as the major product. Pyrolysis of the cyclic sulphites (16) and (17), prepared from the 2,3-exo-diol (4a) by reaction with thionyl chloride, gave mixtures of 2-endo- phenylbornan-3-one (8) and the aldehyde (5).