Ticl4-Catalyzed Addition of Hn3 to Aldehydes and Ketones. Thermolysis and Photolysis of α-Azido Ethers

Alfred Hassner; Richard Fibiger; Ananda S. Amarasekara

doi:10.1021/jo00236a006

Ticl₄-Catalyzed Addition of Hn₃ to Aldehydes and Ketones. Thermolysis and Photolysis of α-Azido Ethers

Alfred Hassner, Richard Fibiger, Ananda S. Amarasekara

Department of Chemistry

Bar-Ilan University

Research output: Contribution to journal › Article › peer-review

30 Scopus citations

Abstract

Aldehydes react with hydrazoic acid and alcohols in the presence of catalytic amounts of TiCl₄ to produce α-azido ethers. The conversion of simple ketones to methyl α-azido alkyl ethers can be accomplished by means of hydrazoic acid and methyl orthoformate. Both gas-phase thermolysis and photolysis of representative a-azido ethers were studied and shown to produce mainly imino ethers. In the thermolysis, migratory preference decreases in the series H » CH₃ > Ph » OR.

Original language	English
Pages (from-to)	22-27
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	53
Issue number	1
DOIs	https://doi.org/10.1021/jo00236a006
State	Published - 1 Jan 1988

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AB - Aldehydes react with hydrazoic acid and alcohols in the presence of catalytic amounts of TiCl4 to produce α-azido ethers. The conversion of simple ketones to methyl α-azido alkyl ethers can be accomplished by means of hydrazoic acid and methyl orthoformate. Both gas-phase thermolysis and photolysis of representative a-azido ethers were studied and shown to produce mainly imino ethers. In the thermolysis, migratory preference decreases in the series H » CH3 > Ph » OR.

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Ticl₄-Catalyzed Addition of Hn₃ to Aldehydes and Ketones. Thermolysis and Photolysis of α-Azido Ethers

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