The Hydrolysis of Vinyl Azides.1 a Comparison with the Schmidt Reaction

Alfred Hassner; E. S. Ferdinandi; R. J. Isbister

doi:10.1021/ja00709a042

The Hydrolysis of Vinyl Azides.1 a Comparison with the Schmidt Reaction

Alfred Hassner, E. S. Ferdinandi, R. J. Isbister

University of Colorado Boulder

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

58 Scopus citations

Abstract

The hydrolysis of representative vinyl azides, 1-azido-1-phenylpropene (3a), 2-azido-3-phenylpropene (3b), and 1-azidoindene (7) was studied in 76% sulfuric acid and diethyl ether. Benzene and dioxane were also used as solvents in the hydrolysis of 7. The products from the hydrolysis were amides and ketones. The same proportion of alkyl and phenyl migration, leading to amides, occurred in the Schmidt reaction of the corresponding ketones under identical conditions, suggesting that the same intermediate is involved in the two reactions.

Original language	English
Pages (from-to)	1672-1675
Number of pages	4
Journal	Journal of the American Chemical Society
Volume	92
Issue number	6
DOIs	https://doi.org/10.1021/ja00709a042
State	Published - 1 Mar 1970
Externally published	Yes

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The Hydrolysis of Vinyl Azides.1 a Comparison with the Schmidt Reaction

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