
%0 Journal Article
%A Coxon, JM 
%A Hartshorn, MP 
%A Lewis, AJ 
%T The preparation and rearrangement of some 2,3-oxygenated 2-phenylbornanes
%J Australian Journal of Chemistry
%D 1971/05/01
%V 24
%N 5
%P 1009-1015
%K 
%R https://doi.org/10.1071/CH9711009
%U https://www.publish.csiro.au/paper/CH9711009 
%X 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). 
