51930-93-9Relevant articles and documents
FAVORSKII-TYPE REARRANGEMENT OF α-CHLORO KETIMINES
De Kimpe, Norbert,Verhe, Roland,De Buyck, Laurent,Moens, Luc,Schamp, Niceas
, p. 1837 - 1840 (1981)
The first examples of the Favorskii-type rearrangement of α-monochloro ketimines are reported.The regiospecific opening of the intermediate cyclopropylideneamines parallels the opening of cyclopropanes under Favorskii-conditions.
O-benzenedisulfonimide as a reusable brnsted acid catalyst for hetero-michael reactions
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano
, p. 758 - 767 (2013/01/15)
The hetero-Michael reactions among various oxygen, sulfur, and nitrogen nucleophiles and ,-unsaturated compounds were carried out in the presence of catalytic amounts of o-benzenedisulfonimide as Brnsted acid organocatalyst. The reaction conditions were very mild, and the yields of target products were good. The catalyst was easily recovered and purified, ready to be used in further reactions. This ability grants economic and ecological advantages. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file.
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.