Issue 19, 2019

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
01 Aug 2019
Accepted
19 Aug 2019
First published
21 Aug 2019

Org. Chem. Front., 2019,6, 3401-3407

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

X. Guo, C. Lv, Q. Mahmood, L. Zhou, G. Xu and Q. Wang, Org. Chem. Front., 2019, 6, 3401 DOI: 10.1039/C9QO00965E

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