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Updated: Jun 16, 2025

Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry
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Imine Metathesis by Silica-Supported Catalysts Using the Methodology of Surface Organometallic Chemistry

Published on: October 18, 2019

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窒素酸化物を用いてアジドフリーなメタロジアゾメタン合成

Robert J Ward1, Mike Jörges1, Henning Remm1

  • 1Faculty of Chemistry and Biochemistry, Ruhr-University Bochum, Universitaetsstrasse 150, Bochum 44801, Germany.

Journal of the American Chemical Society
|August 20, 2024
PubMed
まとめ

研究者は,金属化イリドと窒素酸化物から安定したアルカリ金属ダイアゾメタニドを合成した. この安全な方法は,様々な化学合成のための多用途のダイアゾ化合物を提供します.

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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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Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
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In the Sandmeyer reaction, for example, the diazonio group is replaced by a chloro, bromo,...
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