3-CYANOTHIETE 1,1-DIOXIDE: SYNTHESIS AND CYCLOADDITION REACTIONS

Authors

  • Serhii A. Siryi Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine
  • Svitlana V. Shishkina SSI ''Institute for Single Crystals'', National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine
  • Vadim M. Timoshenko Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine

DOI:

https://doi.org/10.1007/7490

Keywords:

azomethine ylide, 1, 3-butadiene, nitrile, thiete 1, 1-dioxide, [3 2] cycloaddition, [4 2] cycloaddition.

Abstract

A new small reactive molecule – 3-cyanothiete 1,1-dioxide – is introduced into preparative organic chemistry. The title compound has been prepared from thietan-3-one by the addition of trimethylsilyl cyanide to carbonyl group followed by the oxidation of sulfur atom and subsequent dehydration of the thietane 1,1-dioxide intermediate. The reactivity of new thiete 1,1-dioxide was demonstrated on the examples of [3+2] and [4+2] cycloaddition reactions.

Author Biography

Vadim M. Timoshenko, Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Akademika Kukharya St., Kyiv 02094, Ukraine Enamine Ltd., 78 Winston Churchill St., Kyiv 02094, Ukraine

Laboratory of organosulfur compounds

Downloads

Published

2023-08-09

Issue

Vol. 59 No. 6/7 (2023): Ukrainian impact on heterocyclic chemistry after the three decades of independence

Section

Short Communications