
TY  - JOUR
A1  - Gall, RE 
A1  - Taylor, J 
T1  - Acetolytic cleavage of 2&#946;,19-Epoxy-5&#945;-cholestane involving a 1,2-Hydride shift to C2
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 10
SP  - 2249
EP  - 2254
KW  - 
UR  - https://doi.org/10.1071/CH9772249 
N2  - 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). 
ER  -

