Studies in the cyclopropa-arene series: approaches to cyclopropa[a]-naphthalene

Abstract

Whereas treatment of 7,7-dichlorobicyclo[4.1.0]hept-2-ene (2) with potassium t-butoxide yields cyclopropabenzene (4), analogous dehydrochlorination of the 2,3-benzo-analogue (6) does not afford cyclopropa[a]-naphthalene (9). Instead 1-chloromethylnaphthalene (10), 1-t-butoxymethylnaphthalene (11), and the elimination-addition product 1-chloromethylene-1,2,3,4-tetrahydro-2-t-butoxynaphthalene(12) are produced.