[3.2]Metacyclophanes. Transannular Cyclization and Ring Expansion

Nitration of [3.2]metacycIophane-2-carboxylic acid proceeds slowly under mild conditions to give a product of a transannular cyclization, 2-nitro-4, 5-(2'-carboxypropano)-9, 10-dihydrophenanthrene. Dimethyl-2- [3.2Jmetacyclophanylmethanol was transformed via its acetate ester to a mixture of olefins which yielded 2, 3-dimethyl[4.2]metacyclophan-l-ene when subjected to acid catalysis.