
TY  - JOUR
A1  - Siddiqui, AH 
A1  - Baig, MH 
A1  - Lakshmi, C 
T1  - The Beckmann rearrangement of 3&#946;-Chloro-5&#945;-cholestan-7-one oxime and related compounds and the Schmidt reaction of the corresponding ketones
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1977
VL  - 30
IS  - 10
SP  - 2271
EP  - 2275
KW  - 
UR  - https://doi.org/10.1071/CH9772271 
N2  - 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. 
ER  -

