The Journal of Organic Chemistry

Alkylaminonitrobenzenes by vicarious nucleophilic amination with 4-(alkylamino)-1, 2, 4-triazoles

AR Katritzky, KS Laurenzo

Index: Katritzky, Alan R.; Laurenzo, Kathleen S. Journal of Organic Chemistry, 1988 , vol. 53, # 17 p. 3978 - 3982

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Citation Number: 118

Abstract

A series of 4-(alkylamino)-1, 2, 4-triazoles transfer the alkylamino group to the 4-position of nitrobenzene and various 3-substituted nitrobenzenes, with no detectable ortho substitution. By contrast 2-nitrothiophene reacts in the 3-position and 2-nitronaphthalene in the 1- position; 1-nitronaphthalene gives a mixture of products derived from dominant 2-with some 4-substitution. The orientations are discussed and rationalized.