The Journal of Organic Chemistry

Photochemical transformations of small ring heterocyclic compounds. 9. Intramolecular 1, 3-dipolar cycloaddition reactions of alkenyl-subituted nitrile imines

A Padwa, S Nahm, E Sato

Index: Padwa,A. et al. Journal of Organic Chemistry, 1978 , vol. 43, p. 1664 - 1671

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Citation Number: 60

Abstract

A series of nitrile imines bearing alkenyl substituents on the nitrogen atom of the 1, 3 dipole were generated in situ by the photolysis of 2-alkenyl-5-phenyl-substituted tetrazoles or by the base treatment of 1-chlorohydrazones. Intramolecular 1, 3-dipolar cycloaddition leading to substituted pyrazoles was the exclusive reaction observed. When the nitrile imine was generated in the presence of an active dipolarophile, bimolecular 1, 3-dipolar ...