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

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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.

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603137, Nizhny Novgorod, Russian Federation

    A. N. Kornev, V. E. Galperin, Yu. S. Panova, V. V. Sushev, A. V. Cherkasov, A. V. Arapova & G. A. Abakumov

Authors
  1. A. N. Kornev
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  2. V. E. Galperin
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  3. Yu. S. Panova
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  4. V. V. Sushev
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  5. A. V. Cherkasov
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  6. A. V. Arapova
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  7. G. A. Abakumov
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Correspondence to A. N. Kornev.

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Dedicated to Academician of the Russian Academy of Sciences B. A. Trofimov on the occasion of his 80th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2073–2078, November, 2018.

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Kornev, A.N., Galperin, V.E., Panova, Y.S. et al. Reactions of 3а,6a-diaza-1,4-diphosphapentalene with activated acetylenes. Russ Chem Bull 67, 2073–2078 (2018). https://doi.org/10.1007/s11172-018-2331-0

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  • DOI: https://doi.org/10.1007/s11172-018-2331-0

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