Skip to main content
Log in

Chemistry of selected cyclic P(III) compounds possessing a P-Cl bond

  • Published:
Journal of Chemical Sciences Aims and scope Submit manuscript

Abstract

The compounds [CH2(6-t-Bu-4-Me-C6H2O)2]PCl (1), (OCH2CMe2CH2O)-PCl (2), and [ClPN(t-Bu)]2 (3) have been utilized as precursors in the synthesis of (i) new pentacoordinate phosphorus compounds [e.g. CH2(6-t-Bu-4-Me-C6H2O)2 P(NRR′)(O2C6C14), CH2(6-t-Bu-4-Me-C6H2O)2PX[OC(O-i-Pr)N=N(C(O)O-i-Pr)],(ii) cyclic phosphates and their complexes [e.g. imidazolium+CH2(6-t-Bu-4-Me-C6H2O)2PO2 -.MeOH], (iii) new cycloaddition products [e.g. CH2(6-t-Bu-4-Me-C6H2O)2PC(CO2Me)C(CO2Me)C(O)N, (iv) macrocyclic compounds [e.g. [(t-BuN)P]2[-OCH2CMe2CH2O-]h2] and (v) phosphonates [e.g. (OCH2CMe2CH2O)P (O)CH2C(CN)=CHC5H4FeC5H5]. The synthetic and structural aspects of these new products are discussed.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. Sherlock D J, Chandrasekaran A, Day R O and Holmes R R 1997Inorg. Chem. 36 5082

    Article  CAS  Google Scholar 

  2. Muthiah C, Praveen Kumar K, Aruna Mani C and Kumaraswamy K C 2000J.Org. Chem. 65 3733

    Article  CAS  Google Scholar 

  3. Allcock H R 1972Inorg. Synth. 25 8

    Google Scholar 

  4. The stable 8-membered ring system has been utilized by us before for synthesizing a variety of penta and hexacoordinte compounds: Said M A, Pülm M, Herbst-Irmer R and Kumara swamy K C 1996J. Am. Chem. Soc. 118 9841

    Article  CAS  Google Scholar 

  5. Said M A, Pülm M, Herbst-Irmer R and Kumaraswamy K C 1997Inorg. Chem. 36 3044

    Article  Google Scholar 

  6. Trippett S 1976Phosphorus Sulfur 1 89

    Article  CAS  Google Scholar 

  7. Corbridge DEC 1990Phosphorus: An outline of its chemistry, biochemistry and technology 4th edn (Amsterdam: Elsevier) pp 994–1007

    Google Scholar 

  8. Smith D J H 1979 InComprehensive organic chemistry (eds) D H R Barton and V D Ollis (vol. ed.) I O Sutherland (Exeter: Pergamon) vol. 2, pp 1233–1256

  9. Schomburg D, Wermuth U and Schmutzler R 1987Chem. Ber. 120 1713

    Article  CAS  Google Scholar 

  10. Kumaraswamy K C, Holmes J M, Day R O and Holmes R R 1990J. Am. Chem. Soc. 112 6092

    Article  Google Scholar 

  11. Prakasha T K, Burton S D, Day R O and Holmes R R 1992Inorg. Chem. 31 5494

    Article  CAS  Google Scholar 

  12. Highly constrained ring systems are an exception: Huang Y, Arif A M and Bentrude W G 1991J. Am. Chem. Soc. 113 7800

    Article  CAS  Google Scholar 

  13. Kumaraswamy S, Muthiah C and Kumaraswamy K C 2000J. Am. Chem. Soc. 122 964

    Article  CAS  Google Scholar 

  14. Kommana P, Kumaraswamy S, Vittal J J and Kumaraswamy K C 2002Inorg. Chem. 41 2356

    Article  CAS  Google Scholar 

  15. For related reactions see: Arbuzov B A, PolezhaevaN A and Vinogradova V S 1968Izv. Akad. Nauk. SSSR, Ser. Khim. 2525

  16. Gonclaves H, Domroy J R, Chapleur Y, Castro B, Faudet H and Burgada R 1980Phosphorus Sulphur 8 147

    Article  Google Scholar 

  17. Majoral J P, Kraemer R, N Gando M'Pondo T and Navech J 1980Tetrahedron 21 1307

    Article  CAS  Google Scholar 

  18. Jeffrey G A 1997An introduction to hydrogen bonding (Oxford: University Press)

    Google Scholar 

  19. Desiraju G R and Steiner T 1999The weak hydrogen bond in structural chemistry and biology (Oxford: University Press)

    Google Scholar 

  20. Jeffrey G A and Saenger W 1991Hydrogen bonding in biological structures (Berlin: Springer-Verlag)

    Google Scholar 

  21. Kumaraswamy K C, Kumaraswamy S and Kommana P 2001J. Am. Chem. Soc. 123 12642

    Article  CAS  Google Scholar 

  22. Perreault D M and Anslyn E V 1998Angew. Chem., Int. Ed. Engl. 36 432

    Article  Google Scholar 

  23. Page M and Williams A 1997Organic and bioorganic mechanisms (Singapore: Longman) p. 156

    Google Scholar 

  24. Raines R T 1998Chem. Rev. 98 1045

    Article  CAS  Google Scholar 

  25. Derewenda Z S, Lee L and Derewenda U 1995J. Mol. Biol. 252 248

    Article  CAS  Google Scholar 

  26. Ref. 6, pp 959–976

  27. Kumaraswamy S, Kommana P, Satish Kumar N and Kumaraswamy K C 2002J. Chem. Soc.,Chem Commun. 40

  28. Padwa A 19841,3-Dipolar cycloaddition chemistry (New York: Wiley Interscience) vol. 1 & 2

    Google Scholar 

  29. Shore N E 1991Comprehensive organic synthesis (eds) B M Trost and I Fleming (vol. ed.) L A Paquette (Oxford: Pergamon) vol. 5, p. 1155

    Google Scholar 

  30. Beiger K, Tejeda J, Reau R, Dahan F and Bertrand G 1994J. Am. Chem. Soc. 116 8087

    Article  Google Scholar 

  31. Vijjulatha M, Kumaraswamy S, Kumaraswamy K C and Engelhardt U 1999Polyhedron 18 2557

    Article  CAS  Google Scholar 

  32. Kommana P and Kumaraswamy K C 2000Inorg. Chem. 39 4384

    Article  CAS  Google Scholar 

  33. Kommana P and Kumara Swamy K C (to be published)

  34. Kumaraswamy S, Selvi R S and Kumaraswamy K C 1997Synthesis 207

  35. Praveen Kumar K, Muthiah C, Kumaraswamy S and Kumaraswamy K C 2001Tetrahedron Lett. 42 3219

    Article  Google Scholar 

  36. Basavaiah D, Rao P D and Hyma R S 1996Tetrahedron 52 8001

    Article  CAS  Google Scholar 

  37. Senthil Kumar K and Kumaraswamy K C 2001J. Organomet. Chem. 637-639 616

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to K. C. Kumaraswamy.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Kumaraswamy, K.C., Kumaraswamy, S., Kommana, P. et al. Chemistry of selected cyclic P(III) compounds possessing a P-Cl bond. J Chem Sci 114, 367–377 (2002). https://doi.org/10.1007/BF02703827

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF02703827

Keywords

Navigation