Journal of the Chemical Society. Perkin transactions I p. 35 - 37 (1983)
Update date:2022-08-03
Topics:
Hudson, Alan T.
Pether, Michael J.
The condensation of 2,3-dichloro-1,4-naphthoquinone with nitrocyclohexane and t-butyl cyclohexanecarboxylate has been studied.The product resulting from reaction of the quinone with t-butyl cyclohexanecarboxylate, 3-chloro-2-(1-t-butoxycarbonylcyclohexyl)-1,4-naphthoquinone (3), was readily hydrolysed to the corresponding acid (4).Thermal cyclisation of this compound gave rise to the two isomeric quinone lactones naphto<2,3-b>furan-3-spirocyclohexane-2,4,9(3H)-trione (8) and naphtho<1,2-b>furan-3-spirocyclohexane-2,4,5(3H)-trione (10).Procedures were devised which allowed either (8) or (10) to be obtained exclusively.
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