CONCURRENT PATHWAY AND UNEXPECTED PRODUCTS IN THE CuAAC REACTION OF ETHYL PROP-2-YNYL METHYLPHOSPHONATE WITH AROMATIC AZIDES

Authors

  • Nazariy T. Pokhodylo Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005
  • Olga Ya. Shyyka Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005
  • Mykola A. Tupychak Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005
  • Yurii I. Slyvka Department of Inorganic Chemistry, Ivan Franko National University of Lviv, Kyryla i Mefodiya St. 6, Lviv 79005, Ukraine
  • Mykola D. Obushak Department of Inorganic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005

DOI:

https://doi.org/10.1007/4870

Keywords:

azides, phosphonates, 1, 2, 3-triazoles, click reaction, unexpected product

Abstract

The CuI-mediated click reaction of aromatic azides, containing the carboxyl moiety in the ortho position to the azido group, with ethylprop-2-ynyl methylphosphonate proceeded via a concurrent pathway whereby the formation of acrylamides predominated over "classical" cycloaddition products 1,2,3-triazoles. The reaction appears to be specific toward the ortho-carboxyl-substituted aromatic azides, while aryl azides with other substituents do not give the "reduction" products, but form the expected click products: (1-aryl-1H-1,2,3-triazol-4-yl)methyl ethyl methylphosphonates. The reaction mechanism is discussed.

Author Biography

Nazariy T. Pokhodylo, Department of Organic Chemistry, Ivan Franko National University of Lviv, 6 Kyryla i Mefodiya St., Lviv 79005

старший научный сотрудник кафедры органической химии

Downloads

Published

2019-05-22

Issue

Vol. 55 No. 4/5 (2019): In memory of Professor Valerii Dmitrievich Orlov

Section

Original Papers