
%0 Journal Article
%A Coxon, JM 
%A Gibson, JR 
%T The influence of stereochemistry on the dehydration of 5-Acetoxy-8a-methyldecahydronaphthalen-4a-ols
%J Australian Journal of Chemistry
%D 1982/06/01
%V 35
%N 6
%P 1165-1172
%K 
%R https://doi.org/10.1071/CH9821165
%U https://www.publish.csiro.au/paper/CH9821165 
%X The dehydration of (4&#945;,5&#945;,8a&#946;)- and (4a&#945;,5&#945;,8a&#945;)-5-acetoxy-8a-methyldecahydronaphthalen-4a-ol with SOCl2/pyridine and H2SO4/Ac2O/HOAc is reported. For both substrates methyl migration does not compete with 1,2-elimination but for the (4a&#945;,5&#945;,8a&#945;)-alcohol, spiran formation, resulting from migration of Cl to C4a, is observed on reaction with H2SO4/Ac2O/HOAc. The influence of the relative stereochemistry at C4a, C5 and C8a on the course of reactions is discussed. 
