Journal of the Chemical Society. Perkin transactions II p. 1847 - 1852 (1988)
Update date:2022-09-26
Topics:
Avila, David V.
Davies, Alwyn G.
Davison, Ian G. E.
4a-Methyl- and 4a-ethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene have been subjected to singlet oxygen oxygenation, and the various hydroperoxides which are formed have been characterised.Evidence is presented that the 8aβ-alkyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4aα-yl hydroperoxides (I; R=Me or Et) rearrange suprafacially and irreversibly in chloroform at 25 deg C to give only the 4aβ-alkyl-2,3,4,4a,5,6,7,8-octahydronaphthalen-2α-yl hydroperoxides (II).Under the same conditions, the corresponding 8aβ-alkyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4aβ-yl hydroperoxides rearrange much more slowly.
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