OXYGENATED PHENANTHRENES VIA QUINOL KETALS - CYCLIZATION VS MIGRATION

2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromos tyrenes with quinone monoketals followed by acid-mediated cyclization of the resulting p-arylquinol ketals. Substitution at the bromostyrene side-chain or the quinone monoketal ring had only a modest effect on yields, but oxygen substitution on the bromostyrene aromatic nucleus r esulted in a competing 1,2-aryl migration arising during the quinol ke tal cyclization step. The extent of this rearrangement was found to be a function of the Lewis acid/solvent system employed.