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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

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

JM Coxon and NB Lindley

Australian Journal of Chemistry 29(10) 2207 - 2217
Published: 1976

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.

https://doi.org/10.1071/CH9762207

© CSIRO 1976

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