Some aspects of cyclopropa-arene chemistry I. Iminocyclopropa[1]phenanthrenes II. Cyclopropa[a]naphthalene

Abstract

Several aspects of cyclopropa-arene chemistry have been examined. In the first part of this work the decomposition of phenanthraquinone 4-phenyl-3-(phenylimino)semicarbazone and phenanthraquinone 4-p-tolyl-3-(p-tolylimino) semicarbazone failed to yield the appropriate 1-(arylimino) cyclopropa[1] - phenanthrene as reported in the literature. Instead the phenanthraquinone 4-arylsemicarbazones were obtained and their structure confirmed by independent synthesis. An attempt to synthesize cyclopropa[a]naphthalene via a 1,3-elimination route was undertaken in the second part of the work. However the treatment of 1-bromo-2-methoxymethylnaphthalene with n-butyl lithium resulted in the formation of 2-(1'-methoxy) pentylnaphthalene and 2-methoxymethylnaphthalene.