Novel Skeletal Rearrangement of Substituted-2-nitro-1, 3-dienes to 1-Nitro-1,3-dienes: An Easy Access to a New Class of Cyclohexene Derivatives^±

±CDRI Communication No. 5482

Abstract

A number of reactions for evoking skeletal rearrangement in 1-(cyclohex-1′-enyl)-1-nitro-2-substituted phenyl ethenes (1–2) and 1-(3-bromo-cyclohex-1′-enyl)-1-nitro-2-substituted phenyl ethenes (6–7), the model compounds representing 2-nitro-1,3-diene system have been studied for obtaining derivatives of 1-nitro-1,3-dienes. Of these, the reaction of compound 6 with tributyl tin hydride (TBTH) was found to be the most suitable for evoking the desired skeletal rearrangement. Reactions of compounds 1, 2, 6, 7 with sodium azide led to the elimination of the nitro group and resulted in the formation of 4,5-disubstituted 1H-1,2,3-triazoles.

±CDRI Communication No. 5482

Notes

±CDRI Communication No. 5482