SYNTHESIS OF FLUORINATED OCTAHYDRO-2<i>H</i>-CHROMENES IN THE PRESENCE OF THE BF<sub>3</sub>•Et<sub>2</sub>O–H<sub>2</sub>O CATALYTIC SYSTEM

Authors

  • Ирина В. Ильина N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Оксана С. Патрушева N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Дина В. Корчагина N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090
  • Константин П. Волчо N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090
  • Нариман Ф. Салахутдинов N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 Akademika Lavrentieva Ave., Novosibirsk 630090 Novosibirsk State University, 2 Pirogova St., Novosibirsk 630090

DOI:

https://doi.org/10.1007/5757

Keywords:

acid catalysts, boron trifluoride etherate, chromene, isopulegol, monoterpenes, organofluorine compounds, Prins reaction

Abstract

The synthesis of fluorinated octahydro-2H-chromene was carried out using the Prins reaction between the monoterpenoid (–)-isopulegol and carbonyl compounds in the presence of the BF3·Et2O/H2O,system, which acts as both an acid catalyst and a fluorine source. The use of the readily available and easy-to-use BF3·OEt2 reagent makes this method of obtaining fluorine derivatives simple and practical.

Authors: Irina V. Il'ina, Oksana S. Patrusheva, Dina V. Korchagina, Konstantin P. Volcho*, Nariman F. Salakhutdinov

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Published

2020-08-18

Issue

Vol. 56 No. 7 (2020): Synthesis and transformations of heterocycles under electrophilic conditions

Section

Original Papers