STUDIES IN THE CYCLOPROPARENE SERIES - REACTIVITY OF THE 1H-CYCLOPROPA[B]NAPHTHALENYL ANION

Proton abstraction from C1 of 1H-cyclopropa[b]naphthalene (1b) provide s anion (2b) as a highly reactive species that is difficult to interce pt in solution with simple electrophiles. The use of iodomethane, benz ophenone and acetone leads to the corresponding monosubstituted cyclop ropanaphthalene (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 exam ined, but they do not provide simple substitution products.