Base-catalysed rearrangements of bicyclic δ-hydroxy-αβ-enones. Part V.

Ramani, P. V. ; John, J. P. ; Narayanan, K. V. ; Swaminathan, S. (1972) Base-catalysed rearrangements of bicyclic δ-hydroxy-αβ-enones. Part V. Journal of the Chemical Society, Perkin Transactions 1, 1972 . pp. 1516-1519. ISSN 0300-922X

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Official URL: http://pubs.rsc.org/en/Content/ArticleLanding/1972...

Related URL: http://dx.doi.org/10.1039/P19720001516

Abstract

4,4a,5,6,7,8-Hexahydro-5β-hydroxy-4aβ-methylnaphthalen-2(3H)-one (1) and its 4aβ-ethyl analogue (6) rearrange in the presence of base to give a mixture of 4-alkyl-3,4-dihydronaphthalen-1(2H)-one and 4-alkyl-3,4,5,6,7,8-hexahydronaphthalen-1(2H)-one. 4aβ-Ethyl-4,4a,5,6,7,8-hexahydro-5β-hydroxy-5α-vinylnaphthalen-2(3H)-one (7) is similarly converted into 4-ethyl-3,4,6,7,9,10-hexahydrobenzocyclo-octene-1(2H),8(5H)-dione (16).

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