
%0 Journal Article
%A Bolliger, JE 
%A Courtney, JL 
%T The Baeyer-Villiger oxidation of a-substituted cyclic ketones
%J Australian Journal of Chemistry
%D 1964/04/01
%V 17
%N 4
%P 440-446
%K 
%R https://doi.org/10.1071/CH9640440
%U https://www.publish.csiro.au/paper/CH9640440 
%X The Baeyer-Villiger oxidation of 2-chlorocholestan-3-one and 2-bromo-cholestan-3-one gives the corresponding &#945;-halo-lactones (VIIIa) and (VIIIc). The &#945;-bromo-lactone is readily rearranged and converted into 2-methoxycarbonyl-3-oxa-5&#945;-cholestane (Va) by boiling methanol but the &#945;-choloro-lactone is unaffected by this treatment. Both the a-bromo-lactone and the or-chloro-lactone react with alkali to form 2-carboxy-3-oxa-5&#945;-cholestane (Vb). &#945;-Iodocholestan-3-one is unexpectedly converted into cholest-1-en-3-one in about 50% yield by trifluoro-peracetic acid.     2-Bromofriedelan-3-one did not undergo a Baeyer-Villiger reaction under the usual conditions, probably owing to the steric hindrance of the carbonyl group. The per-acid oxidation of 2&#946;-hydroxyfriedelan-3-0110 yielded mainly the 2,3-seco-dicarboxylic acid and a smaller amount of the expected &#945;-hydroxy-lactone. However 2&#946;-acetoxyfriedelan-3-one underwent a Baeyer-Villiger oxidation in the expected fashion to give a high yield of the 2-acetoxy-lactone. 
