Journal of Organic Chemistry p. 22 - 27 (1988)
Update date:2022-07-29
Topics:
Hassner, Alfred
Fibiger, Richard
Amarasekara, Ananda S.
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 α-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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