869-07-8Relevant articles and documents
Bromodimethylsulfonium bromide (BDMS) in ionic liquid: a mild and efficient catalyst for Beckmann rearrangement
Yadav, Lal Dhar S.,Garima,Srivastava, Vishnu P.
scheme or table, p. 739 - 743 (2010/04/05)
Bromodimethylsulfonium bromide (BDMS)-catalyzed Beckmann rearrangement of a variety of ketoximes has been carried out in the imidazolium-based ionic liquid [bmim]PF6 under mild conditions without using any additional cocatalyst or solvent to afford excellent conversion and selectivity. The ionic liquid is recovered and reused for up to three runs without any loss of efficiency.
The Favorskii Rearrangement of α-Chloro Ketimines
Kimpe, Norbert De,Sulmon, Paul,Moeens, Luc,Schamp, Niceas,Declercq, Jean-Paul,Meerssche, Maurice Van
, p. 3839 - 3848 (2007/10/02)
The Favorskii rearrangement of α-chloro ketimines has been studied.It was shown that the base-induced rearrangement of α-chloro ketimines afforded imidates or amides via a mechanism involving 1,3-dehydrochlorination and ring-opening of the resulting cyclopropylideneamines.The ring-opening occurred in such a way as to produce the most stable carbanion.The entire mechanism paralleled the well-known cyclopropanone mechanism of the Favorskii rearrangement of the corresponding oxygen analogues, i.e., α-halo ketones.Evidence has been presented that the semibenzilic-type mechanism is not operative in the cases studied.Depending upon the reaction conditions and the substrate, the Favorskii rearrangement was accompanied by various side reactions including nucleophilic substitution, 1,2-dehydrochlorination, rearrangement via intermediate α-alkoxyaziridines, and self-condensation.