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

Alfred Hassner, Richard Fibiger, Ananda S. Amarasekara

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28 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 languageEnglish
Pages (from-to)22-27
Number of pages6
JournalJournal of Organic Chemistry
Volume53
Issue number1
DOIs
StatePublished - 1 Jan 1988

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