
TY  - JOUR
A1  - Ahmad, MS 
A1  - Pillai, NK 
A1  - Chaudhry, ZH 
T1  - Beckmann rearrangement of some steroid &#945;-hydroxy ring B ketoximes: 5-oxo 5,6-seco nitriles
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1974
VL  - 27
IS  - 7
SP  - 1537
EP  - 1543
KW  - 
UR  - https://doi.org/10.1071/CH9741537 
N2  - Five steroid &#945;-hydroxy ring B ketoximes (1)-(5) were subjected to Beckmann rearrangement using thionyl chloride and potassium hydroxide. In each case the products resulted from second-order Beckmann cleavage. In the case of the dioxime (5), the product obtained was a lactam nitrile (11).The C3-substituted oximes (1) and (2) gave, besides the corresponding nitriles (8) and (9), the chloronitrile (6) and the &#945;,&#946;-unsaturated keto nitrile (7). A probable pathway for the formation of (6) from (1) has been suggested. The mass spectra of the nitriles (6)-(10) showed a pronounced peak at m/e 110, resulting from the McLafferty rearrangement involving a C8 and/C11-hydrogen and the C5-keto function. Interestingly, the mass spectrum of (11) did not show the corresponding peak at m/e 141. 
ER  -

