Dehydration Studies of r-4-Chloro-8a-methyl-trans- and cis-decahydronaphthalen-t-4a-ols

Abstract

Electron-withdrawing substituents at C4 in 8a-methyl-trans-decahydronaphthalen-4a-ol allow methyl migration to compete with 1,2-elimination in H₂SO₄/HOAc/Ac₂O media but not in SOCl₂/ pyridine. Under both these reaction conditions for 4-substituted 8a-methyl-cis-decahydronaphthalen- 4a-ols methyl migration does not compete with 1,2-elimination.