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

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

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56 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 languageEnglish
Pages (from-to)1672-1675
Number of pages4
JournalJournal of the American Chemical Society
Volume92
Issue number6
DOIs
StatePublished - 1 Mar 1970
Externally publishedYes

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