The Journal of Organic Chemistry

Addition of semidione radicals to arenediazonium ions: synthesis of 1, 1-diacyl-2-arylhydrazines

A Clerici, O Porta

Index: Clerici, Angelo; Porta, Ombretta Journal of Organic Chemistry, 1991 , vol. 56, # 24 p. 6813 - 6818

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Citation Number: 2

Abstract

The a-dicarbonyl compounds 1 are selectively reduced to semidione radicals 2 by aqueous Ti", via inner-sphere electron transfer (ET). When an equimolar amount of an arenediazonium salt (3) is present, 2 adds to the nitrogen-nitrogen triple bond of 3 to afford the intermediate am radical cation C, which, depending on the nature of the para substituent of the N-phenyl ring, undergoes rearrangement to al, l-diacyl-2-arylhydrazine (4) or ...