Reaction of arylenedioxytrihalophosphoranes with acetylenes 11. Electronic effect of the substituent in arylacetylene on the reaction rate

A. V. Nemtarev, V. F. Mironov, A. S. Aniskin, D. S. Baranov, E. V. Mironova, D. B. Krivolapov, R. Z. Musin, S. F. Vasilevskii, N. O. Druzhkov, V. K. Cherkasov

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The reactions of 2,2,2-trichlorobenzo-1,3,2-dioxaphosphole and its benzo-substituted derivatives with arylacetylenes containing strong +M-donors and -M-acceptors afford benzo[e]-1,2-oxaphosphinine 2-oxides (phosphacoumarins) in high yields. Studies by the competitive reaction method showed that the reaction rate is sensitive to the electronic nature of the substituent in arylacetylene. Thus, the introduction of +M-donors into the phenyl ring of arylacetylene leads to an increase in the reaction rate, whereas the introduction of -M-acceptors results in its substantial decrease. The molecular and supramolecular structures of selected 2-hydroxyphosphacoumarins and substituted vinylphosphonate, which is generated by the cleavage of the P-heterocycle, were studied by X-ray diffraction.

Original languageEnglish
Pages (from-to)55-70
Number of pages16
JournalRussian Chemical Bulletin
Volume62
Issue number1
DOIs
Publication statusPublished - 1 Jan 2013
Externally publishedYes

Keywords

  • 2,2,2-trichloro-5-methylbenzo-1,3,2-dioxaphosphole
  • 2,2,2-trichlorobenzo-1,3,2-dioxaphosphole
  • 4,7-bis(tert-butyl)-2,2,2- trichlorobenzo-1,3,2-dioxaphosphole
  • arylacetylene
  • benzo[e]-1,2-oxaphosphorinine 2-oxides
  • chlorination of the aromatic ring
  • electronic effect of the substituent
  • ipso-substitution of oxygen
  • reaction rate
  • vinylphosphonate

ASJC Scopus subject areas

  • Chemistry(all)

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  • Cite this

    Nemtarev, A. V., Mironov, V. F., Aniskin, A. S., Baranov, D. S., Mironova, E. V., Krivolapov, D. B., Musin, R. Z., Vasilevskii, S. F., Druzhkov, N. O., & Cherkasov, V. K. (2013). Reaction of arylenedioxytrihalophosphoranes with acetylenes 11. Electronic effect of the substituent in arylacetylene on the reaction rate. Russian Chemical Bulletin, 62(1), 55-70. https://doi.org/10.1007/s11172-013-0008-2