Skip to main content
SpringerLink
Log in

Recent Advances in the Chemistry of Diazaphospholes

  • Chapter
  • First Online:
Phosphorus Heterocycles II

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 21))

Abstract

Diazaphospholes, incorporating two nitrogen atoms (one σ3,λ3 and the other σ2,λ3) in addition to a σ2,λ3-phosphorus in the five-membered ring, constitute a well-investigated category of heterophospholes. Possibility of different combinations of three heteroatoms has made available a number of representatives through different synthetic routes. In this chapter, an account of the reports on the chemistry of diazaphospholes made during the last 10–12 years is presented, which highlights new routes and the use of novel reagents for their synthesis, structural aspects and their reactivity towards cycloaddition and complexation reactions, in particular.

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

Access this chapter

Log in via an institution
Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 169.00
Price excludes VAT (USA)
  • Available as EPUB and PDF
  • Read on any device
  • Instant download
  • Own it forever
Softcover Book
USD 219.99
Price excludes VAT (USA)
  • Compact, lightweight edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info
Hardcover Book
USD 219.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

References

  1. Schmidpeter A (1996) In: Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistry II, vol 4. Pergamon, Oxford, p 771

    Chapter  Google Scholar 

  2. Schmidpeter A (2001) In: Mathey F (ed) Phosphorus-carbon heterocyclic chemistry: the rise of a new domain. Elsevier, Oxford, p 363

    Chapter  Google Scholar 

  3. Ignatova NP, Mel’nikov NN, Shvetsov-Shilovskii NI (1967) Chem Heterocycl Compd 3:601

    Article  Google Scholar 

  4. Schmidpeter A, Karaghiosoff K (1990) In: Regitz M, Scherer OJ (eds) Multiple bonds and low coordination in phosphorus chemistry. Thieme, Stuttgart, p 258

    Google Scholar 

  5. Bansal RK, Karaghiosoff K, Schmidpeter A (1994) Tetrahedron 50:7675

    Article  CAS  Google Scholar 

  6. Bansal RK, Heinicke J (2001) Chem Rev 101:3549

    Article  CAS  Google Scholar 

  7. Bansal RK, Gupta N (2004) In: Storr RC, Gilchrist TL (eds) Science of synthesis: methods of molecular transformations (Houben-Weyl), vol 13. Thieme, Stuttgart, p 689

    Google Scholar 

  8. Bansal RK, Gupta N, Surana A (1998) J Indian Chem Soc 75:648

    CAS  Google Scholar 

  9. Bansal RK, Gupta N, Kumawat SK (2007) Curr Org Chem 11:33

    Article  CAS  Google Scholar 

  10. Regitz M, Binger P (1998) Angew Chem Int Ed Engl 27:1484

    Article  Google Scholar 

  11. Regitz M (1990) Chem Rev 90:191

    Article  CAS  Google Scholar 

  12. Regitz M (1990) In: Regitz M, Scherer OJ (eds) Multiple bonds and low coordination in phosphorus chemistry. Thieme, Stuttgart, p 58

    Google Scholar 

  13. Bansal RK, Karaghiosoff K, Gupta N, Schmidpeter A, Spindler C (1991) Chem Ber 124:475

    Article  CAS  Google Scholar 

  14. Bansal RK, Karaghiosoff K, Gandhi N, Schmidpeter A (1995) Synthesis 361

    Google Scholar 

  15. Bansal RK, Mahnot R, Pandey G, Gupta R (1994) J Indian Chem Soc 71:415

    CAS  Google Scholar 

  16. Bansal RK, Pandey G, Gupta R, Karaghiosoff K, Schmidpeter A (1995) Synthesis 173

    Google Scholar 

  17. Baccolini G, Orsolan G, Mezzina E (1995) Tetrahedron Lett 36:447

    Article  CAS  Google Scholar 

  18. Niessen W (1996) Ph.D. thesis, University of Kaiserslautern, Germany

    Google Scholar 

  19. Guo XY, Wang QR, Tao FG (2004) Chinese J Chem 22:1003

    Article  CAS  Google Scholar 

  20. Tolmachev AA, Dovgopoly SI, Kostyuk AN, Komarov IV, Pinchuk AM (1997) Phosphorus Sulfur Silicon 123:125

    Article  CAS  Google Scholar 

  21. Grobe J, Le Van De Hegemann M, Krebs B, Lage M (1992) Chem Ber 125:411

    Article  CAS  Google Scholar 

  22. Grobe J, Armbrecht A, Van DL, Krebs B, Kuchinke J, Läge M, Würthwein E-U (2001) Z Anorg Allg Chem 627:1241

    Article  CAS  Google Scholar 

  23. Weber L, Kaminski O, Stammler H-G, Neumann B (1995) Organometallics 14:581

    Article  CAS  Google Scholar 

  24. Weber L, Kleinebekel S, Stammler H-G, Stammler A (2002) Z Anorg Allg Chem 628:810

    Article  CAS  Google Scholar 

  25. Weinmair JH, Brunnhuber G, Schmidpeter A (1980) Chem Ber 113:2278

    Article  Google Scholar 

  26. Rösch W, Regitz M (1984) Angew Chem Int Ed Engl 23:900

    Article  Google Scholar 

  27. Rösch W, Facklam T, Regitz M (1987) Tetrahedron 43:3247

    Article  Google Scholar 

  28. Rösch W, Hees U, Regitz M (1987) Chem Ber 120:1645

    Article  Google Scholar 

  29. Sanchez M, Réau R, Marsden CJ, Regitz M, Bertrand G (1999) Chem Eur J 5:274

    Article  CAS  Google Scholar 

  30. Nyulaszi L, Varnai P, Eisfeld W, Regitz M (1997) J Comput Chem 18:609

    Article  CAS  Google Scholar 

  31. Nyulaszi L (2005) J Organomet Chem 690:2597

    Article  CAS  Google Scholar 

  32. Mack A, Pierron E, Allspach T, Bergsträβer U, Regitz M (1998) Synthesis 1305

    Google Scholar 

  33. Ito S, Miyake H, Yoshifuji M (2007) Eur J Inorg Chem 3491

    Google Scholar 

  34. Bourissou D, Floch PLe, Mathey F, Bertrand G (1999) CR Acad Sci Ser IIc Chim 2:351

    CAS  Google Scholar 

  35. Manz B, Maas G (1996) Tetrahedron 52:10053

    Article  CAS  Google Scholar 

  36. Manz B, Bergsträsser U, Kerth J, Maas G (1997) Chem Ber/Recueil 130:779

    Article  CAS  Google Scholar 

  37. Gaumont A-C, Pellerin B, Cabioch J-L, Morise X, Lesvier M, Savignac P, Guenot P, Denis J-M (1996) Inorg Chem 35:6667

    Article  CAS  Google Scholar 

  38. Fontal B, Goldwhite H, Roswel DG (1966) J Org Chem 31:2424

    Article  CAS  Google Scholar 

  39. Schmidpeter A, Willhalm A (1984) Angew Chem Int Ed Engl 23:903

    Article  Google Scholar 

  40. Schmidpeter A (1986) Phosphorus Sulfur 28:71

    Article  CAS  Google Scholar 

  41. Polborn K, Schmidpeter A, Märkl G, Wilhalm A (1999) Z Naturforsch 54B:187

    Google Scholar 

  42. Schrödel H-P, Schmidpeter A (1997) Chem Ber Recueil 130:89

    Article  Google Scholar 

  43. Szarvas L, Bajko Z, Fusz S, Burck S, Daniels J, Nieger M, Gudat D (2002) Z Anorg Allg Chem 628:2303

    Article  CAS  Google Scholar 

  44. Fiedler W, Regitz M, Bertrand G (1997) Bull Soc Chim Belg 106:455

    CAS  Google Scholar 

  45. Litvinov IA, Naumov VA, Gryaznova TV, Pudovik AN, Kibardin AM (1990) Dokl Akad Nauk SSR 312:623

    CAS  Google Scholar 

  46. Denk MK, Gupta S, Ramachandran R (1996) Tetrahedron Lett 37:9025

    Article  CAS  Google Scholar 

  47. Carmalt CJ, Lomeli V, McBurnett BG, Cowley AH (1997) Chem Comm 2095

    Google Scholar 

  48. Sauers RR (1997) Tetrahedron 53:2357

    Article  CAS  Google Scholar 

  49. Gudat D, Haghverdi A, Hupfer H, Nieger M (2000) Chem Eur J 6:3414

    Article  CAS  Google Scholar 

  50. Burck S, Gudat D, Nättinen K, Nieger M, Niemeyer M, Schmid D (2007) Eur J Inorg Chem 5112

    Google Scholar 

  51. Benkő Z, Burck S, Gudat D, Nieger M, Nyulászi L, Shore N (2008) Dalton Trans 4937

    Google Scholar 

  52. Denk MK, Gupta S, Lough AJ (1999) Eur J Inorg Chem 41

    Google Scholar 

  53. Kibardin AM, Litvinov IA, Naumov VA, Struchkov YT, Gryaznova TV, Mikhailov YB, Pudovik AN (1988) Dokl Akad Nauk SSR 298:369

    CAS  Google Scholar 

  54. Gudat D, Haghverdi A, Nieger M (2000) Angew Chem Int Ed Engl 39:3084

    CAS  Google Scholar 

  55. Burck S, Gudat D, Nieger M, Du Mont W-W (2006) J Am Chem Soc 128:3946

    Article  CAS  Google Scholar 

  56. Gudat D, Haghverdi A, Nieger M (2001) Phosphorus Sulfur Silicon 168:203

    Article  Google Scholar 

  57. Schmidpeter A, Lochschmidt S, Sheldrick WS (1982) Angew Chem Int Ed Engl 21:63

    Article  Google Scholar 

  58. Reeske G, Hoberg CR, Hill NJ, Cowley AH (2006) J Am Chem Soc 128:2800

    Article  CAS  Google Scholar 

  59. Reeske G, Cowley AH (2007) Inorg Chem 46:1426

    Article  CAS  Google Scholar 

  60. Ellis BD, Macdonald CLB (2007) Inorg Chim Acta 360:329

    Article  CAS  Google Scholar 

  61. Malavaud C, Boisden MT, Charbonnel Y, Barrans J (1979) Tetrahedron Lett 20:447

    Article  Google Scholar 

  62. Malavaud C, N’Gando M’Pondo T, Lopez L, Barrans J, Legros J-P (1984) Can J Chem 62:43

    Article  CAS  Google Scholar 

  63. Burford N, Dipchand AI, Royan BW, White PS (1989) Acta Crystallogr Sect C: Cryst Struct Commun 45:1485

    Article  Google Scholar 

  64. Schmid D, Loscher S, Gudat D, Bubrin D, Hartenbach I, Scheild T, Benkő Z, Nyulászi L (2009) Chem Commun 830

    Google Scholar 

  65. Karaghiosoff K, Cleve C, Schmidpeter A (1986) Phosphorus Sulfur 28:289

    Article  CAS  Google Scholar 

  66. Schmidpeter A, Bansal RK, Karaghiosoff K, Steinmüller F, Spindler C (1990) P S Si 49/50:349

    Google Scholar 

  67. Karaghiosoff K, Schmidpeter A, Mayer P (1996) In: Herrmann WA (ed) Synthetic methods of inorganic and organometallic chemistry; Group 15: phosphorus and organometallic chemistry, vol 3. Thieme, Stuttgart, p 52

    Google Scholar 

  68. Litvinov IA, Karaghiosoff K, Schmidpeter A, Zabotina EY, Dianova EN (1991) Heteroat Chem 2:369

    Article  CAS  Google Scholar 

  69. Karaghiosoff K, Mahnot R, Cleve C, Gandhi N, Bansal RK, Schmidpeter A (1995) Chem Ber 128:581

    Article  CAS  Google Scholar 

  70. Bansal RK, Kabra V, Gupta N (1992) Indian J Chem 31B:254

    CAS  Google Scholar 

  71. Bansal RK, Mahnot R, Sharma DC, Karaghiosoff K, Schmidpeter A (1992) Heteroat Chem 3:351

    Article  CAS  Google Scholar 

  72. Gupta N, Jain CB, Heinicke J, Bharatiya N, Bansal RK, Jones PG (1998) Heteroat Chem 9:333

    Article  CAS  Google Scholar 

  73. Karaghiosoff K, Bansal RK, Gupta N (1992) Z Naturforsch 47B:373

    Google Scholar 

  74. Bansal RK, Mahnot R, Sharma DC, Karaghiosoff K (1992) Synthesis 267

    Google Scholar 

  75. Bansal RK, Kabra V, Munjal R, Gupta N (1994) Indian J Chem 33B:992

    CAS  Google Scholar 

  76. Bansal RK, Sharma DC, Mahnot R (1991) Tetrahedron Lett 32:6433

    Article  CAS  Google Scholar 

  77. Bansal RK, Kabra V, Munjal R, Gupta N (1994) Phosphorus Sulfur Silicon 97:141

    Article  CAS  Google Scholar 

  78. Claramunt RM, Lopez C, Schmidpeter A, Willhalm A, Elguero J, Alkorta I (2001) Spectroscopy 15:27

    CAS  Google Scholar 

  79. Wan L, Alkorta I, Elguero J, Sun J, Zheng W (2007) Tetrahedron 63:9129

    Article  CAS  Google Scholar 

  80. Marsh RE (2002) Acta Crystallogr 58B:893

    Google Scholar 

  81. Mikoluk MD, McDonald R, Cavell RG (1999) Inorg Chem 38:4056

    Article  CAS  Google Scholar 

  82. Mikoluk MD, McDonald R, Cavell RG (1999) Organometallics 18:3306

    Article  CAS  Google Scholar 

  83. Mikoluk MD, McDonald R, Cavell RG (1999) Inorg Chem 38:2791

    Article  CAS  Google Scholar 

  84. Gupta N, Garg R, Babu NJ, Bansal RK (results to be published)

    Google Scholar 

  85. Gudat D (1997) Coord Chem Rev 163:71

    Article  CAS  Google Scholar 

  86. Nyulászi L, Veszprémi L, Réffy J (1993) J Phys Chem 97:4011

    Article  Google Scholar 

  87. Gupta N, Bansal RK (2003) J Indian Chem Soc 80:997

    CAS  Google Scholar 

  88. Bansal RK, Gupta N, Pandey G (results to be published)

    Google Scholar 

  89. Khusainova N, Garipova G, Zyablikova T, Cherkasov R, Pudovik A (2002) Phosphorus Sulfur Silicon 177:2231

    Article  CAS  Google Scholar 

  90. Khusainova NG, Zverev V, Garipova G, Cherkasov R, Pudovik A (2002) Phosphorus Sulfur Silicon 177:2229

    Article  CAS  Google Scholar 

  91. Zverev VV, Khusainova NG, Reshetkova GR, Cherkasov RA (2000) Russian J Gen Chem 70:399

    CAS  Google Scholar 

  92. Khusainova NG, Reshetkova GR, Irtuganova EA, Cherkasov RA (2000) Russian J Gen Chem 70:154

    CAS  Google Scholar 

  93. Mironov VF, Khusainova NG, Reshetkova GR, Zyablikova TA, Cherkasov RA (2000) Russian J Gen Chem 70:984

    CAS  Google Scholar 

  94. Khusainova NG, Mostovaya OA, Cherkasov RA (2006) Russian J Gen Chem 76:495

    Article  CAS  Google Scholar 

  95. Khusainova NG, Mostovaya OA, Azancheev NM, Litvinov IA, Krivolapov DB, Cherkasov RA (2004) Mandeleev Comm 14:212

    Article  Google Scholar 

  96. Bansal RK, Gupta N, Bharatiya N, Gupta G, Surana A, Hackenbracht G, Karaghiosoff K (1998) Heteroat Chem 9:445

    Article  CAS  Google Scholar 

  97. Bansal RK, Gupta N, Gupta N (2004) Heteroat Chem 15:271

    Article  CAS  Google Scholar 

  98. Bansal RK, Kumawat SK (2008) Tetrahedron 64:10945

    Article  CAS  Google Scholar 

  99. Bansal RK, Karaghiosoff K, Gupta N, Gandhi N, Kumawat SK (2005) Tetrahedron 61:10521

    Article  CAS  Google Scholar 

  100. Bansal RK, Karaghiosoff K, Gupta N, Kabra V, Mahnot R, Sharma DC, Munjal R, Kumawat SK (2005) Z Naturforsch 60B:7

    Google Scholar 

  101. Bansal RK, Gupta N, Kumawat SK (2006) Tetrahedron 62:1548

    Article  CAS  Google Scholar 

  102. Bansal RK, Gupta N, Kumawat SK (2006) Heteroat Chem 17:402

    Article  CAS  Google Scholar 

  103. Kerth J, Maas G (1999) Eur J Org Chem 2633

    Google Scholar 

  104. Kerth J, Maas G (2001) Eur J Org Chem 1581

    Google Scholar 

  105. Guo X, Feng Li, Tao F (2006) J Chem Res 2:130

    Article  Google Scholar 

  106. Guo X, Feng Li, Wang Q, Zhiming L, Tao F (2006) J Heterocycl Chem 43:353

    Article  CAS  Google Scholar 

  107. Jikyo T, Schatz J, Maas G (2003) J Phys Org Chem 16:504

    Article  CAS  Google Scholar 

  108. Kraaijkamp JG, Grove DM, Koten GV, Schmidpeter A (1988) Inorg Chem 27:2612

    Article  CAS  Google Scholar 

  109. Kraaijkamp JG, Grove DM, Koten GV, Ernsting JM, Schmidpeter A, Goubitz K, Stam CH, Schenk H (1997) Inorg Chim Acta 265:47

    Article  CAS  Google Scholar 

  110. Zheng W, Zhang G, Fan K (2006) Organometallics 25:1548

    Article  CAS  Google Scholar 

  111. Yorke J, Wan J, Xia A, Zheng W (2007) Tetrahedron Lett 48:8843

    Article  CAS  Google Scholar 

  112. Wan L, Pi C, Zhang L, Zheng W, Weng L, Chen Z, Zhang Y (2008) Chem Comm 2266

    Google Scholar 

  113. Pi C, Wan L, Gu Y, Zheng W, Weng L, Chen Z, Wu L (2008) Inorg Chem 47:9739

    Article  CAS  Google Scholar 

  114. Pi C, Wan L, Weiping L, Pan Z, Wu H, Wang Y, Zheng W, Weng L, Chen Z, Wu L (2009) Inorg Chem 48:2967

    Article  CAS  Google Scholar 

  115. Mikoluk MD, Cavell RG (1999) Inorg Chem 38:1971

    Article  CAS  Google Scholar 

Download references

Acknowledgment

The author acknowledges financial support from the Department of Science and Technology (DST), New Delhi.

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Rajasthan, Jaipur, 302 004, India

    Neelima Gupta

Authors
  1. Neelima Gupta
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Neelima Gupta .

Editor information

Editors and Affiliations

  1. Dept. Chemistry, University of Rajasthan, Jaipur, 302004, India

    Raj K. Bansal

Rights and permissions

Reprints and permissions

Copyright information

© 2010 Springer-Verlag Berlin Heidelberg

About this chapter

Cite this chapter

Gupta, N. (2010). Recent Advances in the Chemistry of Diazaphospholes. In: Bansal, R. (eds) Phosphorus Heterocycles II. Topics in Heterocyclic Chemistry, vol 21. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2009_20

Download citation

Publish with us

Policies and ethics

Search

Navigation