Synthesis 2018; 50(04): 711-722
DOI: 10.1055/s-0036-1589155
short review
© Georg Thieme Verlag Stuttgart · New York

tert-Butyl Nitrite (TBN) as a Versatile Reagent in Organic Synthesis

Pengfei Li
a   College of Chemistry & Chemical Engineering, Northwest Normal University, Anning East Road 967, Lanzhou, Gansu 730070, P. R. of China
,
Xiaodong Jia*
a   College of Chemistry & Chemical Engineering, Northwest Normal University, Anning East Road 967, Lanzhou, Gansu 730070, P. R. of China
b   School of Chemistry & Chemical Engineering, Yangzhou University, Siwangting Road 180, Yangzhou, Jiangsu 225002, P. R. of China   Email: 1803546575@qq.com   Email: jiaxd1975@163.com
› Author Affiliations
We thank the Natural Science Foundation of China (NSFC, No. 21362030 and 21562038) for supporting our research.
Further Information

Publication History

Received: 27 October 2017

Accepted after revision: 22 November 2017

Publication Date:
14 December 2017 (online)


Abstract

tert-Butyl nitrite (TBN) is an important metal-free reagent that is widely applied in various organic transformations. Besides its traditional applications in nitrosation and diazotization, its ability to activate molecular oxygen to enable the initiation of radical reactions, including nitration, oximation, oxidation, and so on, has attracted extensively attention in the past decade. This review highlights recent advances in this field to promote further exploration of this versatile compound.

1 Introduction

2 Reactions Involving TBN

2.1 Nitrosation

2.2 Oximation

2.3 Diazotization

2.4 Nitration

2.5 Oxidation

2.6 Other Reactions

3 Conclusion and Perspective

 
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