
%0 Journal Article
%A Coxon, JM 
%A Lindley, NB 
%T Dehydration studies of 8a-Methyldecahydronaphthalen-4a-ols
%J Australian Journal of Chemistry
%D 1976/10/01
%V 29
%N 10
%P 2207-2217
%K 
%R https://doi.org/10.1071/CH9762207
%U https://www.publish.csiro.au/paper/CH9762207 
%X The H2SO4-HOAc-Ac2O-catalysed dehydration of the epimeric 8a-methyldecahydronaphthalen-4a- ols has been shown to occur regiospecifically without skeletal or methyl migration, by loss of a proton syn to the departing anionic moiety. The results are interpreted in terms of the intermediacy of a tight ion pair where the oxy anion acts as the base in the removal of the proton. The introduction of an  electron-withdrawing substituent at Cl, syn to the 8a-methyl of 8a-methyl-trans-decahydronaphthalen-4a-ol, allows methyl migration to compete with 1,2-elimination. 
