Reactions of arylenedioxytrihalophosphoranes with acetylenes 14. Methoxyphenylacetylenes in the reaction with 2,2,2-trichlorobenzo-1,3,2-dioxaphosphole

A. V. Nemtarev, V. F. Mironov, A. S. Aniskin, D. S. Baranov, D. B. Krivolapov, R. Z. Musin, S. F. Vasilevskii

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Abstract

Reactions of 2,2,2-trichlorobenzo-1,3,2-dioxaphosphole with 2-, 3-, 4-methoxyphenyl-, 3,4-dimethoxyphenyl- and 2,3,4-trimethoxyphenylacetylenes furnished 4-phenylbenzo-1,2-oxaphosphinine derivatives. The presence of one, two, or three donor methoxy groups in the aromatic ring of phenylacetylene does not change the general direction of the reaction which is characteristic of arylacetylenes and lead to 4-arylareno-1,2-oxaphosphinine derivatives. The presence of substituents in the exocyclic aryl group at ortho-position to the oxaphosphinine ring led to the appearance of atropoisomers.

Original languageEnglish
Pages (from-to)1299-1307
Number of pages9
JournalRussian Chemical Bulletin
Volume65
Issue number5
DOIs
Publication statusPublished - 1 May 2016
Externally publishedYes

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Keywords

  • 2,2,2-trichlorobenzo-1,3,2-dioxaphosphole
  • atropoisomerism
  • benzo-[e]-1,2-oxaphosphinine 2-oxides
  • chlorination of aromatic ring
  • formation of P—C bond
  • ipso-substitution of oxygen
  • methoxyphenylacetylenes

ASJC Scopus subject areas

  • Chemistry(all)

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