A new mechanism for the beckmann rearrangement of ketoximes

Henry Stephen, Benjamin Staskun

Research output: Contribution to journalArticleResearchpeer-review

Abstract

Based on experimental observations, a new mechanism is proposed for the Beckmann rearrangement involving the formation of a ketoxime anhydride by dehydration of two molecules of the ketoxime. The anhydride rearranges to give the ketoxime imidate which further rearranges forming the imidoyl anhydride which in the presence of hydrogen chloride gives an imidoyl chloride and an amide in equimolecular proportions.

LanguageEnglish
Pages962-970
Number of pages9
JournalJournal of the Chemical Society (Resumed)
Publication statusPublished - 1956

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Oximes
Anhydrides
Imidoesters
Hydrochloric Acid
Dehydration
Amides
Chlorides
Molecules

Cite this

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title = "A new mechanism for the beckmann rearrangement of ketoximes",
abstract = "Based on experimental observations, a new mechanism is proposed for the Beckmann rearrangement involving the formation of a ketoxime anhydride by dehydration of two molecules of the ketoxime. The anhydride rearranges to give the ketoxime imidate which further rearranges forming the imidoyl anhydride which in the presence of hydrogen chloride gives an imidoyl chloride and an amide in equimolecular proportions.",
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A new mechanism for the beckmann rearrangement of ketoximes. / Stephen, Henry; Staskun, Benjamin.

In: Journal of the Chemical Society (Resumed), 1956, p. 962-970.

Research output: Contribution to journalArticleResearchpeer-review

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AU - Stephen, Henry

AU - Staskun, Benjamin

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AB - Based on experimental observations, a new mechanism is proposed for the Beckmann rearrangement involving the formation of a ketoxime anhydride by dehydration of two molecules of the ketoxime. The anhydride rearranges to give the ketoxime imidate which further rearranges forming the imidoyl anhydride which in the presence of hydrogen chloride gives an imidoyl chloride and an amide in equimolecular proportions.

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