Solvent-controlled chemoselective N-dealkylation-N-nitrosation or C-nitration of N-alkyl anilines with tert-butyl nitrite?

Organic Chemistry Frontiers Pub Date: 2019-08-21 DOI: 10.1039/C9QO00965E

Abstract

A metal-free, acid-free and chemoselective N-dealkylation-N-nitrosation or C-nitration of N-alkyl anilines has been developed. tert-Butyl nitrite (TBN) efficiently promotes the synthesis of N-nitrosoanilines, nitroanilines and N-nitroso-nitroanilines with good to excellent yields and chemoselectivities. The selective reduction of N-nitrosoanilines and N-nitroso-nitroanilines was smoothly achieved, affording phenylhydrazine, 2-nitroaniline and 1,2-benzenediamine derivatives.

Graphical abstract: Solvent-controlled chemoselective N-dealkylation-N-nitrosation or C-nitration of N-alkyl anilines with tert-butyl nitrite
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