Synthesis of azobenzenes from quinone acetals and arylhydrazines.

M. Carreño,Gerardo Fernández Mudarra,E. Merino,M. Ribagorda

Published 2004 in Journal of Organic Chemistry

ABSTRACT

Direct reaction between quinone bisacetals and arylhydrazines gives azobenzenes. The presence of catalytic amounts of cerium ammonium nitrate strongly accelerates the reaction. When the bisacetal has a substituent at the 2,5-cyclohexadiene framework, only one regioisomer is formed. The method represents a simple, mild, and novel synthetic access to differently substituted azocompounds in high to excellent yield.

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