Effect of electronic factors on 1,3-dipolar cycloaddition of 2,4,6-triazidopyridines to <i>tert</i>-butylphosphaacetylene

Abstract

2,4,6-Triazido-3-chloro-5-cyanopyridine and 2,4,6-triazido-3,5-dicyanopyridine react with tert-butylphosphaacetylene with formation of the corresponding 2,4, 6-tris(3H-1, 2, 3, 4-triazaphospholo)pyridnes. The first step of both reactions is regioselective cycloaddition of the phosphaalkyne to the azido groups in the 4 position of the pyridine ring. The electronic properties of the substituents on the pyridine ring of the azidopyridines exert a significant effect both on the reactivity of the monoadduct intermediates and on the properties of the end products of 1,3-dipolar tris-cycloaddition.

How to Cite
Chapyshev, S. V.; Bergsträßer, U.; Regitz, M. Chem. Heterocycl. Compd. 1996, 32, 59. [Khim. Geterotsikl. Soedin. 1996, 67.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01169355