Tetrahedron

Oxygenated phenanthrenes via quinol ketals: Cyclization vs. migration

GW Morrow, TM Marks, DL Sear

Index: Morrow, Gary W.; Marks, Tina M.; Sear, Debra L. Tetrahedron, 1995 , vol. 51, # 37 p. 10115 - 10124

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Citation Number: 15

Abstract

2-methoxyphenanthrenes were prepared by reaction of lithiated 2-bromostyrenes with quinone monoketals followed by acid-mediated cyclization of the resulting p-arylquinol kelals. 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. ...

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