132400-01-2Relevant academic research and scientific papers
Thermal rearrangement of N-alkyl-, and N-aryl-(2,2-dihalo-1-phenylcyclopropyl)methyleneamines to 1-alkyl-, and 1-aryl-2 (or 3)-halo-4-phenylpyrroles
Kagabu,Tsuji,Kawai,Ozeki
, p. 341 - 349 (2007/10/02)
The thermolysis of N-t-alkyl-, and N-aryl-(2,2-dichlorocyclopropyl)methyleneamines yielded directly 1-t-alkyl, and 1-aryl-3-chloropyrroles as the major products along with a slight amount of the 2-chloro isomers. The transformation to the 3-chloropyrroles was enhanced in polar solvents. But basic additives directed the thermal rearrangement into the 1,2-bond cleavage of the cyclopropane ring, leading to the 2-chloropyrroles. On the other hand, (difluorocyclopropyl)methyleneamines were pyrolyzed exclusively to 3-fluoropyrroles under 1,3-bond cleavage. The ionic mechanism involving a heterolytic dissociation of chlorine atom under 1,3-bond scission of the cyclopropane ring is proposed for the rearrangement to 3-chloropyrroles, while a homolytic cleavage pathway is proposed for 3-fluoropyrroles. The present thermolysis supplies a unique preparative tool for 2-, and 3-halo-4-phenylpyrrole derivatives.
2- and 3-chloropyrroles and process for preparing the same
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, (2008/06/13)
Novel 2- or 3-chloropyrroles represented by the general formula: STR1 wherein R1 represents hydrogen atom, chlorine atom, alkyl group, or aryl group which may optionally be substituted, with the proviso that any one of the two groups represente
Manipulated Thermal Rearrangement of N-t-Alkyl-2,2-dichlorocyclopropylimines to N-Alkyl-chloropyrroles
Kagabu, Shinzo,Kawai, Itsumi
, p. 1393 - 1394 (2007/10/02)
Thermolysis of N-t-butyl- and N-cumyl-2,2-dichlorocyclopropylimines gives selectively 3-chloropyrroles in polar solvents and 2-chloro derivatives with added base.
