Studies in the Cycloproparene Series:Reactivity of the 1H-Cyclopropa[b]naphthalenyl Anion.

Abstract

Proton abstraction from C1 of 1H-cyclopropa[b]naphthalene (1b) provides anion (2b) as a highly reactive species that is difficult to intercept in solution with simple electrophiles. The use of iodomethane, benzophenone and acetone leads to the corresponding monosubstituted cyclopropanaphthalene (7)–(9), but only in modest yields. The reaction with benzophenone provides a complementary but less convenient route to the methylidenecyclopropanaphthalene (5b; R′ = R′′ = Ph). Reactions of (2b) with benzyl halides, acid chlorides and esters have also been examined, but they do not provide simple substitution products.