
%0 Journal Article
%A Siddiqui, AH 
%A Baig, MH 
%A Lakshmi, C 
%T The Beckmann rearrangement of 3&#946;-Chloro-5&#945;-cholestan-7-one oxime and related compounds and the Schmidt reaction of the corresponding ketones
%J Australian Journal of Chemistry
%D 1977/10/01
%V 30
%N 10
%P 2271-2275
%K 
%R https://doi.org/10.1071/CH9772271
%U https://www.publish.csiro.au/paper/CH9772271 
%X The chromic acid oxidation of cholesteryl chloride gave 3&#946;- chlorocholest-5-en-7-one, which on hydrogenation gave 3&#946;-chloro-5&#945;- cholestan-7-one. The Schmidt reaction of this ketone afforded a single lactam, 3&#946;-chloro-7a-aza-B-homo-5&#945;-cholestan-7-one. The Beckmann rearrangement of its oxime by means of thionyl chloride or p- toluenesulphonyl chloride and pyridine gave the same lactam. The structure of the lactam was established by its conversion into a known lactam by reduction. 3&#946;-Chlorocholest-5-en-7-one oxime on treatment with thionyl chloride or the corresponding O-tosyloxime on passing through a column of alumina underwent Beckmann rearrangement to give a single lactam, 3&#946;-chloro-7&#945;-aza-B-homocholest-5-en-7-one. 
