
%0 Journal Article
%A Baigent, DR 
%A Lewis, KG 
%T Supposed acetyl migration from the 3&#946;- to the 19-hydroxyl group in &#916;<sup>5</sup>-steroids
%J Australian Journal of Chemistry
%D 1974/02/01
%V 27
%N 2
%P 323-329
%K 
%R https://doi.org/10.1071/CH9740323
%U https://www.publish.csiro.au/paper/CH9740323 
%X The product of monotritylation of 3&#946;,19-dihydroxyandrost-5-en-17-one is the 3&#946;-trityl ether, not the 19-trityl ether as previously proposed. In consequence the product of acetylation of the monotrityl ether is 19-acetoxy-3&#946;-trityloxyandrost-5-en-17-one and thus acid-catalysed detritylation of this compound yields directly the 19-acetoxy derivative without the invoking of an acid-catalysed rearrangement. The isomeric 3&#946;-hydroxy-19-trityloxyandrost-5-en-17-one has been prepared as well as a number of 3&#946;-tritylated &#916;5-steroids which have been used to study the influence of the trityl ether group upon p.m.r. chemical shifts in this series. 
