Solvent-controlled chemoselective N-dealkylation-N-nitrosation or C-nitration of N-alkyl anilines with tert-butyl nitrite
Literature Information
Publication Date
2019-08-21
DOI
10.1039/C9QO00965E
Impact Factor
5.281
Authors
Qaiser Mahmood, Guangqiang Xu, Qinggang Wang
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
![(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure](https://static.chemtradehub.com/structs/865/865689-24-3-5fef.webp "(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid structure")
(1R,6R)-6-({[(2-Methyl-2-propanyl)oxy]carbonyl}amino)-3-cyclohexene-1-carboxylic acid
CAS Number:
865689-24-3
Molecular Formula:
C12H19NO4
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