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Russian Chemical Bulletin

, Volume 67, Issue 11, pp 2073–2078 | Cite as

Reactions of 3а,6a-diaza-1,4-diphosphapentalene with activated acetylenes

  • A. N. KornevEmail author
  • V. E. Galperin
  • Yu. S. Panova
  • V. V. Sushev
  • A. V. Cherkasov
  • A. V. Arapova
  • G. A. Abakumov
Full Articles
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Abstract

The reaction of cyclohexane-annulated 3 a,6a-diaza-1,4-diphosphapentalene (DDP) with di-tert-butyl acetylenedicarboxylate (DBAD) affords the 1,3-dipolar cycloaddition product of the acetylene moiety to the phosphorus and sp2-carbon atoms of DDP in 90% yield. No individual products were isolated in the reaction of DDP with dimethyl acetylenedicarboxylate (DMAD). In the three-component DDP–DMAD–carbazole system (1: 2: 1), a product was generated in 73% yield via successive reactions, including the 1(P),3(C)-dipolar cycloaddition of DMAD to DDP, the addition of the second equivalent of DMAD to the three-coordinate phosphorus atom of the intermediate, and the NH addition of carbazole at the unsaturated C=C bond of the second DMAD moiety. The structures of the reaction products were established by X-ray diffraction.

Key words

heterophospholes heteropentalenes phosphorus ylides carbenoids alkynes organophosphorus compounds 

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • A. N. Kornev
    • 1
    Email author
  • V. E. Galperin
    • 1
  • Yu. S. Panova
    • 1
  • V. V. Sushev
    • 1
  • A. V. Cherkasov
    • 1
  • A. V. Arapova
    • 1
  • G. A. Abakumov
    • 1
  1. 1.G. A. Razuvaev Institute of Organometallic ChemistryRussian Academy of SciencesNizhny NovgorodRussian Federation

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