
%0 Journal Article
%A Ahmad, MS 
%A Pillai, NK 
%A Chaudhry, ZH 
%T Beckmann rearrangement of some steroid &#945;-hydroxy ring B ketoximes: 5-oxo 5,6-seco nitriles
%J Australian Journal of Chemistry
%D 1974/07/01
%V 27
%N 7
%P 1537-1543
%K 
%R https://doi.org/10.1071/CH9741537
%U https://www.publish.csiro.au/paper/CH9741537 
%X 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. 
