Rearrangement of epoxides. Part 2. The preparation and rearrangement of some epoxides of 2,2-dimethylbicyclo[4.3.0]non-1(9)-enes carrying substituents at C(3) and C(6)

Abstract

The preparation of 3α,9α-epoxy-4,4-dimethylhexahydroindan-5β,8β-carbolactone (17), ethyl 3α,9α-epoxy-4,4-dimethyl-5-oxahexahydroindane-8β-carboxylate (20), ethyl 3β,9β-epoxy-4,4-dimethyl-5-oxohexahydroindane-8β-carboxylate (21), 3β,9β-epoxy-8β-hydroxymethyl-4,4-dimethylhexahydroindan-5β-ol (19), and a mixture of the α- and β-epoxides of 4,4,8-trimethyl-1,6,7,8-tetrahydro-2H-inden-5(4H)-one (24) and (25) are described. Their rearrangements with boron trifluoride–diethyl ether complex have been carried out and the major products identified. Each rearrangement proceeds by a different pathway.