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.
|Number of pages||4|
|Journal||Journal of the Chemical Society, Perkin Transactions 1|
|State||Published - 1 Jan 1976|
ASJC Scopus subject areas
- Chemistry (all)