Title

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

Document Type

Article

Publication Date

1-1-1988

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. © 1988, American Chemical Society. All rights reserved.

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