Australian Journal of Chemistry

Dehydration studies of 8a-Methyldecahydronaphthalen-4a-ols

JM Coxon, NB Lindley

Index: Coxon,J.M.; Lindley,N.B. Australian Journal of Chemistry, 1976 , vol. 29, p. 2207 - 2217

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Citation Number: 4

Abstract

Abstract The H 2 SO 4-HOAc-Ac 2 O-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 ...