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Facile Preparation of 4-Substituted Quinazoline Derivatives
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Published on: February 15, 2016

The mechanism and kinetics of decomposition of 5-aminotetrazole

Jian-Guo Zhang1, Li-Na Feng, Shao-Wen Zhang

  • 1State Key Laboratory of Explosion Science and Technology, Beijing Institute of Technology, Beijing 100081, PR China. zhangjianguobit@yahoo.com.cn

Journal of Molecular Modeling
|March 12, 2008
PubMed

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Nitrous acid is a relatively weak and unstable acid prepared in situ by the reaction of sodium nitrite and cold, dilute hydrochloric acid. In an acidic solution, the nitrous acid undergoes protonation when it loses water to form a nitrosonium ion—an electrophile. Nitrous acid reacts with primary amines to give diazonium salts. The reaction is called diazotization of primary amines.
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In the presence of an aqueous base and a halogen, primary amides can lose the carbonyl (as carbon dioxide) and undergo rearrangement to form primary amines. This reaction, called the Hofmann rearrangement, can produce primary amines (aryl and alkyl) in high yields without contamination by secondary and tertiary amines.
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The Hofmann and Curtius rearrangement reactions can be applied to synthesize primary amines from carboxylic acid derivatives such as amides and acyl azides. In the Hofmann rearrangement, a primary amide undergoes deprotonation in the presence of a base, followed by halogenation to generate an N-haloamide. A second proton abstraction produces a stabilized anionic species, which rearranges to an isocyanate intermediate via an alkyl group migration from the carbonyl carbon to the neighboring...