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

Авторы

  • Nazariy T. Pokhodylo Львовский национальный университет имени Ивана Франко
  • 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

Ключевые слова:

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

Аннотация

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.

Биография автора

Nazariy T. Pokhodylo, Львовский национальный университет имени Ивана Франко

старший научный сотрудник кафедры органической химии

Загрузки

Опубликован

2019-05-22

Выпуск

Том 55 № 4/5 (2019): Памяти профессора Валерия Дмитриевича Орлова

Раздел

Оригинальные статьи