Stereoselectivity in the formation and allylic rearrangement of 8a-methyl- and 8a-ethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalenyl hydroperoxides
- 1 January 1988
- journal article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 2
- No. 10,p. 1847-1852
- https://doi.org/10.1039/p29880001847
Abstract
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 °C to give only the 4aβ-alkyl-2,3,4,4a,5,6,7,8,8-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. [graphic omitted]Keywords
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