Fragmentation of 3-oximino-4-chromanone

Heating either the methanesulfonate ester of 3-oximino-4-chromanone or 3-oximino-4-chromanone and an alternative acylating agent such as p-toluensulfonyl chloride or acetic anhydride in the presence of aqueous base afforded two major fragments: salicyclic acid and 2-carboxyphenoxyacetonitrile. These...

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Bibliographic Details
Published inJournal of pharmaceutical sciences Vol. 65; no. 3; p. 397
Main Authors Wormser, H C, Lieu, S Y
Format Journal Article
LanguageEnglish
Published United States 01.03.1976
Subjects
Acetamides
Acetonitriles
Chemical Phenomena
Chemistry
Chromones
Mesylates
Oximes
Phenoxyacetates
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Summary:Heating either the methanesulfonate ester of 3-oximino-4-chromanone or 3-oximino-4-chromanone and an alternative acylating agent such as p-toluensulfonyl chloride or acetic anhydride in the presence of aqueous base afforded two major fragments: salicyclic acid and 2-carboxyphenoxyacetonitrile. These compounds are derived from two separate cleavage pathways involving the acylated oxime. In one pathway, fragmentation appears to be assisted by the ether ring oxygen; in the other, it is assisted by the alpha-carbonyl group of the oxime ester.
ISSN:0022-3549
DOI:10.1002/jps.2600650320