
%0 Journal Article
%A Gall, RE 
%A Taylor, J 
%T Acetolytic cleavage of 2&#946;,19-Epoxy-5&#945;-cholestane involving a 1,2-Hydride shift to C2
%J Australian Journal of Chemistry
%D 1977/10/01
%V 30
%N 10
%P 2249-2254
%K 
%R https://doi.org/10.1071/CH9772249
%U https://www.publish.csiro.au/paper/CH9772249 
%X Acetolytic cleavage of 2&#946;,19-epoxy-5&#945;-cholestane (1a) with boron trifluoride and acetic anhydride followed by hydrolysis gave the 2&#945;,19- diol (2b), the only rearrangement product the 1&#945;,19-diol (3b) and a mixture of olefins (4b). Deuterium exchange studies and the use of a paramagnetic shift reagent have shown that the reaction leading to the rearranged diol(3b) is not concerted and appears to involve an intermediate carbonium ion since hydride shift from both C 1 and C 3 occur. The formation of the 1&#945;,19-diol (3b) as the only rearranged product can be rationalized as nucleophilic attack on the acetoxonium ion (8). 
