Synthesis of polycyclic aromatic hydrocarbons via a novel annelation method

RG Harvey, C Cortez, SA Jacobs

Index: Harvey, Ronald G.; Cortez, Cecilia; Jacobs, Stephen A. Journal of Organic Chemistry, 1982 , vol. 47, # 11 p. 2120 - 2125

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Citation Number: 28

Abstract

A new general synthetic approach to polycyclic aromatic hydrocarbons is described. The method is based on the convenient availability of o-lithioarylamides from regiospecific metalation of Nfl-diethylarylamides with alkyllithium-amine reagents. Addition of the o- lithioarylamide to an aryl ketone or aldehyde affords a lactone. Reduction of the latter with zinc and alkali or HI generates the free acid which undergoes cyclization with ZnClz and ...