CONDENSATION PRODUCTS OF MONO- AND DIBROMO-SUBSTITUTED METHYL VINYL SULFONES WITH CH-ACIDS ENOLATES

Authors

  • В. А. Васин N. P. Ogarev Mordovian State University, Saransk 430000
  • И. Ю. Болушева N. P. Ogarev Mordovian State University, Saransk 430000
  • В. В. Разин St. Petersburg State University, St. Petersburg 198504

DOI:

https://doi.org/10.1007/7020

Keywords:

CH-acids enolates, tetrahydrothiophene-S, S-dioxide, 2-phenylethenyl sulfones, ethylidenemalononitrile, heterocyclization, Michael reaction, Ramberg-Bäcklund reaction

Abstract

Bromomethyl (E)-2-phenylethenyl and bromomethyl (Z)-1-bromo-2-phenylethenyl sulfones undergo condensation with enolates generated from malononitrile, dimethyl malonate, methyl and ethyl acetoacetate using NaH in THF to give tetrahydrothiophene S,S-dioxides. Methyl (E)-1-bromo-2-phenylethenyl and methyl (E)-2-bromo-2-phenylethenyl sulfones react with sodium malononitrile to give 2-[2-(methylsulfonyl)-1-phenylethylidene]malononitrile. The bromomethyl-(E)-2-bromo-2-phenyl ethenyl sulfone reacts with sodium malononitrile to give 2-[2-(bromomethylsulfonyl)-1-phenylethylidene]malononitrile exclusively.

How to Cite
Vasin, V. A.; Bolusheva, I. Yu.; Razin, V. V.  Chem. Heterocycl. Compd. 2008, 44, 419. [Khim. Geterotsikl. Soedin. 2008, 539.]

For this article in the English edition see DOI 10.1007/s10593-008-0058-9


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Published

2022-09-01

Issue

No. 4 (2008)

Section

Original Papers