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Synlett 2011(8): 1184-1185  
DOI: 10.1055/s-0030-1259948
SPOTLIGHT
© Georg Thieme Verlag Stuttgart ˙ New York

tert-Butyl Nitrite

Yang Liu*
Faculty of Pharmacy, School of Medicine, Xi’an Jiaotong University, West Yanta Road 76, Xi’an, Shanxi 710061, P. R. of China
e-Mail: Liuyang_1125@yahoo.com.cn;
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Publication History

Publication Date:
20 April 2011 (online)

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Introduction

tert-Butyl nitrite (TBN) is a very useful synthetic reagent with requisite chemical and physical properties, such as volatizing with a low boiling point and favorable solubility, which leads to the feasibility of mixing or separating with other reagents. TBN is an efficient NO source, frequently used as the reagent for diazotization [¹] and nitros­ation of alcohols, thiols, amines and cycloalkanes. [²-5] It is also a safe and chemoselective nitrating agent that provides preferentially mononitro derivatives. [6] Besides, TBN is used in oxidations due to its ability to activate molecular oxygen. [7] TBN could be prepared in good to excellent yield by treating tert-butyl alcohol with nitrous acid or other nitrosating agents, such as nitrosyl chloride in ­pyridine and nitrosonium salts (NO+BF4 -, NO+ClO4 -). In the laboratory, usually sodium nitrite and sulfuric acid is used instead of nitrous acid (Scheme  [¹] ). [8] An overview of the usage of TBN in organic synthesis is presented below.

Scheme 1 Preparation of TBN