Alkylation, acylation, and Beckmann rearrangement of oximes in the presence of an oxidation-reduction system

Shmuel Bittner, Sarina Grinberg

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

The system triphenylphosphine-diethyl azodiformate (TPP-DAF) can interact with oximes in the presence of either carboxylic acids or alcohols. Reactions of benzophenone oxime with a variety of aromatic carboxylic acids lead to O-acyl derivatives which undergo spontaneous Beckmann rearrangement. This modification of the Beckmann rearrangement takes place under very mild (0°C), aprotic (tetrahydrofuran), and weakly acidic conditions, affording NN-diacyl aromatic amines as final products. The reaction of benzophenone oxime with alcohols in the presence of TPP-DAF gives O-alkyl ethers of the oxime. A mechanism is proposed.

Original languageEnglish
Pages (from-to)1708-1711
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Issue number16
DOIs
StatePublished - 1 Jan 1976

ASJC Scopus subject areas

  • Chemistry (all)

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