Abstract
The dehydration of (4α,5α,8aβ)-
and (4aα,5α,8aα)-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 (4aα,5α,8aα)-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.
Cited by
3 articles.
订阅此论文施引文献
订阅此论文施引文献，注册后可以免费订阅5篇论文的施引文献，订阅后可以查看论文全部施引文献
1. Spirocyclics;Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy;1987
2. Bicyclo[4.4.0]decanes;Stereochemical Analysis of Alicyclic Compounds by C-13 NMR Spectroscopy;1987
3. An investigation of the conformational dynamics of ion-pair intermediates in the syn-elimination of 8a-methyldecahydronaphthalen-4a-ols;Tetrahedron;1984-01