TY - JOUR
T1 - Alkylation, acylation, and Beckmann rearrangement of oximes in the presence of an oxidation-reduction system
AU - Bittner, Shmuel
AU - Grinberg, Sarina
PY - 1976/1/1
Y1 - 1976/1/1
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=37049106147&partnerID=8YFLogxK
U2 - 10.1039/p19760001708
DO - 10.1039/p19760001708
M3 - Article
AN - SCOPUS:37049106147
SP - 1708
EP - 1711
JO - Journal of the Chemical Society, Perkin Transactions 1
JF - Journal of the Chemical Society, Perkin Transactions 1
SN - 0300-922X
IS - 16
ER -