Abstract
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.
Cited by
13 articles.
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