Reaction of 2-nitro and 3-nitro-2-cyclohexenone acetals: Preparation of useful intermediates

Article abstract of DOI:10.1016/S0040-4020(01)96113-7

Preparation of 2-nitro-2-cyclohexenone acetal 31 starting from 2-nitrocyclohexanone acetal 29 has been reported for the first time. This compound as well as 3-nitro-2-cyclohexenone acetal 1, whose synthesis has been reported by us earlier, react with a variety of nucleophiles to form highly functionalised intermediates. One of them viz. 21 is converted into a bicyclic α-methylene-γ-lactone 24 using radical chemistry.