Some attempted syntheses of cyclopropa[1] phenanthrene

Abstract

The present study has been directed towards investigating possible syntheses of cyclopropa[1]phenanthrene via (I) the 3H-indazole route, from 1,3-dipolar addition of diphenyldiazomethane to 9,10-dehydrophenanthrene. The work describes the attempts made at generating 9, 10-dehydrophenanthrene from (a) metallised 9-chlorophenanthrene, (b) 9-aminophenanthrene-10-carboxylic acid, and (c) 9-aminophenanthrene; (II) a 1,3-elimination from 9-bromo-10-methoxymethylphenanthrene using n-butyllithium.