
TY  - JOUR
A1  - Coxon, JM 
A1  - Gibson, JR 
T1  - The influence of stereochemistry on the dehydration of 5-Acetoxy-8a-methyldecahydronaphthalen-4a-ols
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1982
VL  - 35
IS  - 6
SP  - 1165
EP  - 1172
KW  - 
UR  - https://doi.org/10.1071/CH9821165 
N2  - The dehydration of (4&#945;,5&#945;,8a&#946;)- and (4a&#945;,5&#945;,8a&#945;)-5-acetoxy-8a-methyldecahydronaphthalen-4a-ol with SOCl2/pyridine and H2SO4/Ac2O/HOAc is reported. For both substrates methyl migration does not compete with 1,2-elimination but for the (4a&#945;,5&#945;,8a&#945;)-alcohol, spiran formation, resulting from migration of Cl to C4a, is observed on reaction with H2SO4/Ac2O/HOAc. The influence of the relative stereochemistry at C4a, C5 and C8a on the course of reactions is discussed. 
ER  -

