
TY  - JOUR
A1  - Coxon, JM 
A1  - Lindley, NB 
T1  - Dehydration studies of 8a-Methyldecahydronaphthalen-4a-ols
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1976
VL  - 29
IS  - 10
SP  - 2207
EP  - 2217
KW  - 
UR  - https://doi.org/10.1071/CH9762207 
N2  - 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. 
ER  -

