Unusual Chlorination During an Epoxidation Reaction of an Ethenocyclopropa[b]naphthalene Derivative

Abstract

The structure of (1α,1aα,2β,7aα,8R,9R)-8,9-dichloro-1a,2,7,7a-tetrahydro-2,7-ethano-1H-cyclopropa[b]napthalene-1-carbonitrile, C 14 H 11 Cl 2 N, consists of two nonplanar six-membered carbon rings (constituting a [2.2.2] bicyclic system), one of which shares two C atoms with a benzene ring and has two Cl substituents ; the other is fused to a cyclopropane ring carrying a C=N substituent. The two Cl atoms of the -C-C(Cl)-C(Cl)-C- bridging system have an anti arrangement with respect to the plane of the four C atoms.