142011-03-8Relevant articles and documents
Oxygenated phenanthrenes via quinol ketals: Cyclization vs. migration
Morrow, Gary W.,Marks, Tina M.,Sear, Debra L.
, p. 10115 - 10124 (2007/10/02)
2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromostyrenes 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 resulted in a competing 1,2-aryl migration arising during the quinol ketal cyclization step. The extent of this rearrangement was found to be a function of the Lewis acid/solvent system employed.