122801-53-0Relevant academic research and scientific papers
Thermal Rearrangement of N-Arylmethyl- and N-Alkyl-2,2-dihalogenocyclopropyl Imines
Kagabu, Shinzo,Ando, Chihaya,Ando, Junko
, p. 739 - 752 (2007/10/02)
An extended study of the thermal isomerization of 1-substituted 2,2-dihalogenocyclopropyl imines is reported.The thermolysis of N-arylmethyl-2,2-dichlorocyclopropanecarbaldimines 15a-h produces 2-aryl- 16a-h and 2-aryl-4-chloro-pyridine derivatives 17a-h, while N-cyclopropyl imines 15i, j yielded N-alyklchloropyrroles.The 2,2-dibromocyclopropane analogue undergoes thermolysis at lower temperatures.An ionic mechanism triggered by the halide ion dissociation is proposed for the thermal rearrangement on the basis of a study using deuterated imine 15m, and the effects of additives and solvents.On the other hand, difluorocyclopropyl imine undergoes a homolytic cleavage of cyclopropane 1,3-bond with lower activation energy than the dichlorocyclopropyl imine, and afforded the N-alykl-3-fluoropyrrole derivative preferentially.
