Skip to main content
SpringerLink
Log in

Synthesis of tricyclic spirophosphoranes via reaction of 2-(4,5-dihydrofuran-3-yl)-N-phenyl-1,3,2-oxazaphospholidine with C,N-diarylnitrile imines

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

Unique tricyclic compounds with a five-coordinate phosphorus atom shared by three rings, 7-aryl-3′,5-diphenyl-3,5-dihydro-2H-spiro[1,2-oxaphospholo[2,3-d][1,2,4]diazaphosphinine-8,2′-[1,3,2]oxazaphospholidines], have been synthesized for the first time via reaction of 2-(4,5-dihydrofuran-3-yl)-3-phenyl-1,3,2-oxazaphospholidine with C,N-diarylnitrile imines. Presumably, these compounds are formed via a three-step process including generation of P+-C=N-N− dipolar ion, intramolecular N−→C= cyclization with simultaneous opening of the dihydrofuran ring, and closure of oxaphospholane ring.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Trishin, Yu.G., Chistokletov, V.N., and Petrov, A.A., Sov. Sci. Rev., Sect. B, 1991, vol. 15,part 5, p. 1.

    Google Scholar 

  2. Namestnikov, V.I., Trishin, Yu.G., and Bel’skii, V.K., Russ. J. Gen. Chem., 1996, vol. 66, no. 8, p. 1367.

    Google Scholar 

  3. Trishin, Yu.G., Namestnikov, V.I., and Bel’skii, V.K., Russ. J. Gen. Chem., 1999, vol. 69, no. 5, p. 736.

    CAS  Google Scholar 

  4. Trishin, Yu.G., Namestnikov, V.I., and Bel’skii, V.K., Russ. Chem. Bull., Int. Ed., 2000, vol. 49, no. 1, p. 129. DOI: 10.1007/BF02499078.

    Article  CAS  Google Scholar 

  5. Trishin, Yu.G., Namestnikov, V.I., and Gonchar, T.V., Russ. Chem. Bull., Int. Ed., 2005, vol. 54, no. 7, p. 1637. DOI: 10.1007/s11172-006-0016-6.

    Article  CAS  Google Scholar 

  6. Platonov, A.Yu., Trostyanskaya, I.G., Kazankova, M.A., and Chistokletov, V.N., Zh. Obshch. Khim., 1982, vol. 52, no. 2, p. 268.

    CAS  Google Scholar 

  7. Ramirez, F., Patwardhan, A.V., Kugler, H.J., and Smith, C.P., J. Am. Chem. Soc., 1967, vol. 89, p. 6276. DOI: 10.1021/ja01000a051; Ramirez, F., Gubati, A.S., and Smith, C.P., J. Am. Chem. Soc., 1967, vol. 89, p. 6283. DOI: 10.1021/ja01000a052.

    Article  CAS  Google Scholar 

  8. Namestnikov, V.I., Tamm, L.A., Trishin, Yu.G., and Chistokletov, V.N., Zh. Obshch. Khim., 1987, vol. 57, no. 6, p. 1412; Erofeeva, M.R., Trishin, Yu.G., and Chistokletov, V.N., Zh. Obshch. Khim., 1989, vol. 59, no. 9, p. 2146; Namestnikov, V.I., Trishin, Yu.G., Tamm, L.A., and Chistokletov, V.N., Zh. Obshch. Khim., 1990, vol. 60, no. 3, p. 510; Senyukh, S.M., Namestnikov, V.I., Trishin, Yu.G., and Chistokletov, V.N., Zh. Obshch. Khim., 1990, vol. 60, no. 8, p. 1926; Trishin, Yu.G., Afanasov, A.F., Litvinov, I.A., Naumov, V.A., and Chistokletov, V.N., Zh. Obshch. Khim., 1990, vol. 60, no. 11, p. 2446.

    CAS  Google Scholar 

  9. Huisgen, R., Seidel, M., Wallbillich, G., and Knupfer, H., Tetrahedron, 1962, vol. 17, nos. 1–2, p. 3. DOI: 10.1016/S0040-4020(01)99001-5.

    Article  CAS  Google Scholar 

  10. Tietze, L.-F. and Eicher, T., Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschungslaboratorium, Stuttgart: Georg Thieme, 1991, 2nd ed.

    Book  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. St. Petersburg State Technological University of Plant Polymers, ul. Ivana Chernykh 4, St. Petersburg, 198095, Russia

    Yu. G. Trishin & V. I. Namestnikov

Authors
  1. Yu. G. Trishin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. I. Namestnikov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yu. G. Trishin.

Additional information

Original Russian Text © Yu.G. Trishin, V.I. Namestnikov, 2015, published in Zhurnal Obshchei Khimii, 2015, Vol. 85, No. 2, pp. 289–293.

To the 80th Anniversary of B.I. Ionin

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Trishin, Y.G., Namestnikov, V.I. Synthesis of tricyclic spirophosphoranes via reaction of 2-(4,5-dihydrofuran-3-yl)-N-phenyl-1,3,2-oxazaphospholidine with C,N-diarylnitrile imines. Russ J Gen Chem 85, 462–466 (2015). https://doi.org/10.1134/S1070363215020176

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363215020176

Keywords

Search

Navigation