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Aromatic Phosphorus Heterocycles

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Part of the book series: Topics in Heterocyclic Chemistry

Abstract

Phosphorus an element with an electronegativity somewhat less than that of carbon and is an excellent and versatile building block of aromatic systems. Thus, in many systems carbon can be replaced efficiently by phosphorus. The versatility is a consequence of the many different bonding modes available for the pnicogen element. The extent of the aromaticity is different with the different bonding modes, and can also be fine tuned by utilizing various substituents that have inductive or steric effects. It is noteworthy that even small effects can have a large impact on the chemistry of these compounds. Thus, the analysis of subtle changes in aromaticity can be of importance in the future.

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Abbreviations

AIM:

Atoms in molecules;

ARCS: :

Aromatic ring current shielding;

ASE:

Aromatic stabilization energy;

B3LYP:

Becke three-parameter hybrid functional combined with Lee–Yang–Parr correlation functional;

BDSHRT:

Bond shortening index;

BI:

Bird index;

CASPT2:

Complete active space with second-order perturbation theory;

CASSCF:

Complete active space – self-consistent field method;

CID:

Collision-induced dissociation;

DFT:

Density functional theory;

DME:

Dimethoxyethane;

ELF:

Electron localization function;

EPR:

Electron paramagnetic resonance;

GIAO:

Gauge-including atomic orbital;

GIMIC:

Gauge-including magnetically induced current;

HF:

Hartree–Fock method;

HOMA:

Harmonic oscillator model of aromaticity;

ISE:

Isomeric stabilization energy;

KS:

Kohn–Sham (orbital);

Mes*:

2,4,6-Tri-tert-butylphenyl (supermesityl);

NICS:

Nucleus independent chemical shift;

NHC:

N-Heterocyclic carbenes:

RE:

Resonance energy;

SBA:

Sum of bond angles;

VB:

Valence bond

References

  1. Regitz M, Scherer O (eds) (1990) Multiple bonding and low coordination in phosphorus chemistry. Thieme, Stuttgart

    Google Scholar 

  2. Mathey F, Nixon JF, Dillon K (1998) Phosphorus: the carbon copy. Wiley, New York

    Google Scholar 

  3. Mathey F (ed) (2001) Phosphorous–carbon heterocyclic chemistry. The rise of a new domain. Pergamon, Oxford

    Google Scholar 

  4. Nyulászi L (2001) Chem Rev 101:1229

    PubMed  Google Scholar 

  5. Mathey F (2003) Angew Chem Int Ed Engl 42:1578

    PubMed  CAS  Google Scholar 

  6. Blush JA, Chen P, Wiedmann RT, White MG (1993) J Chem Phys 98:3557

    ADS  CAS  Google Scholar 

  7. Berkowitz J, Curtiss LA, Gibson ST, Greene JP, Hillhouse GL, Pople JA (1986) J Chem Phys 84:375

    ADS  CAS  Google Scholar 

  8. Koopmans T (1934) Physica 1:104

    ADS  Google Scholar 

  9. Kimura K, Katsumata S, Achiba Y, Yamazaki T, Iwata S (1980) Handbook of HeI photoelectron spectra. Halsted, New York

    Google Scholar 

  10. Lacombe S, Gonbeau D, Cabioch J-L, Pellerin B, Denis J-M, Pfister-Guillouzo G (1988) J Am Chem Soc 110:6964

    CAS  Google Scholar 

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

    Google Scholar 

  12. Schmidt MW, Troung P, Gordon MS (1987) J Am Chem Soc 109:5217

    CAS  Google Scholar 

  13. Schleyer PvR, Kost DMW (1988) J Am Chem Soc 110:2105

    CAS  Google Scholar 

  14. Modelli A, Hajgató B, Nixon JF, Nyulászi L (2004) J Phys Chem A 108:7440

    CAS  Google Scholar 

  15. Bourissou D, Guerret O, Gabbai FP, Bertrand G (2000) Chem Rev 100:39

    PubMed  CAS  Google Scholar 

  16. Kirmse W (2004) Angew Chem Int Ed Engl 43:1767

    PubMed  CAS  Google Scholar 

  17. Canac Y, Soleilhavoup M, Conejero S, Bertrand G (2004) J Organomet Chem 689:3857

    CAS  Google Scholar 

  18. Hahn FE (2006) Angew Chem Int Ed Engl 45:1348

    PubMed  CAS  Google Scholar 

  19. Herrmann WA, Schütz JA, Frey GD, Herdtweck E (2006) Organometallics 25:2437

    CAS  Google Scholar 

  20. Enders D, Niemeier O, Henseler A (2007) Chem Rev 107:5606

    PubMed  CAS  Google Scholar 

  21. Arduengo AJ, Harlow RL, Kline M (1991) J Am Chem Soc 113:361

    CAS  Google Scholar 

  22. Arnold PL, Pearson S (2007) Coord Chem Rev 251:596

    CAS  Google Scholar 

  23. Boeme C, Frenking G (1996) J Am Chem Soc 118:2039

    Google Scholar 

  24. Heinemann C, Müller T, Apeloig Y, Schwartz H (1996) J Am Chem Soc 118:2023

    CAS  Google Scholar 

  25. Cheng M-J, Hu C-H (2001) Chem Phys Lett 349:477

    ADS  CAS  Google Scholar 

  26. Cowley AH, Kemp R (1985) Chem Rev 85:367

    CAS  Google Scholar 

  27. Sanchez M, Mazières MR, Lamandé L, Wolf R (1990) In: Regitz M, Scherer O (eds) Multiple bonds and low coordination chemistry in phosphorus chemistry.Thieme, Stuttgart

    Google Scholar 

  28. Gudat D (1997) Coord Chem Rev 173:71

    Google Scholar 

  29. Schoeller WW, Tubbesing U (1995) J Mol Struct (THEOCHEM) 343:49

    Article  CAS  Google Scholar 

  30. Gudat D (1998) Eur J Inorg Chem 1087

    Google Scholar 

  31. Malar PEJ (1992) J Org Chem 57:3694

    CAS  Google Scholar 

  32. Mathey F (1994) Coord Chem Rev 137:1

    CAS  Google Scholar 

  33. Dransfeld A, Nyulászi L, Schleyer PvR (1998) Inorg Chem 37:4413

    PubMed  CAS  Google Scholar 

  34. Pimentel GC (1951) J Chem Phys 19:446

    ADS  CAS  Google Scholar 

  35. Hach RJ, Rundle RE (1951) J Am Chem Soc 73:4321

    CAS  Google Scholar 

  36. Reed AE, Schleyer PvR (1990) J Am Chem Soc 112:1434

    CAS  Google Scholar 

  37. Magnusson E (1993) J Am Chem Soc 115:1051

    CAS  Google Scholar 

  38. Johnson WA (1993) Ylides and imines of phosphorous. Wiley, New York

    Google Scholar 

  39. Kolodiazhnyi OI (1999) Phosphorus ylides. Wiley, Weinheim

    Google Scholar 

  40. Nyulászi L, Veszprémi T, Réffy J (1995) J Phys Chem 99:10142

    Google Scholar 

  41. Sanchez-Gonzalez A, Martinez-Garcia H, Melchor S, Dobado JA (2004) J Phys Chem A 108:9188

    CAS  Google Scholar 

  42. Nyulászi L, Veszprémi T (1996) J Phys Chem 100:6456

    Google Scholar 

  43. Schwerdtfeger P, Laakkonen L, Pyykkö P (1992) J Chem Phys 96:6807

    ADS  CAS  Google Scholar 

  44. Nyulászi L, Belghazi A, Kis-Szétsi S, Veszprémi T, Heinicke J (1994) J Mol Struct (THEOCHEM) 313:73

    Google Scholar 

  45. Kapp J, Schade C, El-Nahasa AM, Schleyer PvR (1996) Angew Chem Int Ed Engl 35:2236

    Google Scholar 

  46. Nyulászi L (2000) Tetrahedron 56:79

    Google Scholar 

  47. Schleyer PvR (guest editor) (2001) Chem Rev 101:1115

    PubMed  CAS  Google Scholar 

  48. Schleyer PvR (guest editor) (2005) Chem Rev 105:3433

    CAS  Google Scholar 

  49. Balaban AT, Oniciu DC, Katritzky AR (2004) Chem Rev 104:2778

    Google Scholar 

  50. Baumgartner T, Réau R (2006) Chem Rev 106:4681

    PubMed  CAS  Google Scholar 

  51. Hobbs MG, Baumgartner T (2007) Eur J Inorg Chem, p 3611

    Google Scholar 

  52. Baldridge KK, Siegel JS (2004) J Phys Org Chem 17:740

    CAS  Google Scholar 

  53. Jug K, Koster AM (1991) J Phys Org Chem 4:163

    CAS  Google Scholar 

  54. Jug K, Oniciu DC, Katritzky AR (2001) Chem Rev 101:1421

    PubMed  Google Scholar 

  55. Katritzky AR, Karekon M, Sild S, Kygowski TM, Jug K (1998) J Org Chem 63:5228

    CAS  Google Scholar 

  56. Cyranski MK, Krygowski TM, Katritzky AR, Schleyer PvR (2002) J Org Chem 67:1333

    PubMed  CAS  Google Scholar 

  57. Hess BA Jr, Schaad LJ (1971) J Am Chem Soc 93:2413

    CAS  Google Scholar 

  58. Schleyer PvR, Freeman P, Jiao H, Goldfuss B (1995) Angew Chem Int Ed Engl 34:337

    CAS  Google Scholar 

  59. Cyranski MK, Schleyer PvR, Krygowski TM, Jiao H, Hohlneicher G (2003) Tetrahedron 59:1657

    CAS  Google Scholar 

  60. Schleyer PvR, Pühlhofer F (2002) Org Lett 4:2873

    PubMed  CAS  Google Scholar 

  61. Nyulászi L, Hollóczki O, Lescop C, Hissler M, Réau R (2006) Org Biomol Chem 4:996

    PubMed  Google Scholar 

  62. Hehre WJ, Ditchfield R, Radom L, Pople JA (1970) J Am Chem Soc 92:4796

    CAS  Google Scholar 

  63. George P, Tratchman M, Bock CW, Brett AM (1976) J Chem Soc Perkin II, p 1222

    Google Scholar 

  64. Cyransky MK (2005) Chem Rev 105:3773

    Google Scholar 

  65. Nyulászi L, Keglevich G, Quin LD (1996) J Org Chem 61:7808

    PubMed  Google Scholar 

  66. Bird CW (1985) Tetrahedron 41:1409

    CAS  Google Scholar 

  67. Bird CW (1990) Tetrahedron 46:5697

    CAS  Google Scholar 

  68. Kruszewski J, Krygowski TM (1972) Tetrahedron Lett 3839

    Google Scholar 

  69. Nyulászi L, Várnai P, Veszprémi T (1995) J Mol Struct (THEOCHEM) 358:55

    Google Scholar 

  70. Meyer LH, Saika A, Gutowski HS (1953) J Am Chem Soc 75:4567

    CAS  Google Scholar 

  71. Bernstein HJ, Schneider WG, Pople JA (1956) Proc R Soc London A 236:515

    Article  ADS  CAS  Google Scholar 

  72. Pople JA (1956) J Chem Phys 24:1111

    ADS  CAS  MathSciNet  Google Scholar 

  73. Jiao H, Schleyer PvR (1995) J Am Chem Soc 117:11529

    CAS  Google Scholar 

  74. Dauben HJ Jr, Wilson JD, Laity L (1968) J Am Chem Soc 90:811

    CAS  Google Scholar 

  75. Dauben HJ Jr, Wilson JD, Laity L (1969) J Am Chem Soc 91:1991

    CAS  Google Scholar 

  76. Schleyer PvR, Jiao H (1996) Pure Appl Chem 68:209

    CAS  Google Scholar 

  77. Schleyer PvR, Maerker C, Dransfeld A, Eikema Hommes NJRv (1996) J Am Chem Soc 118:6317

    CAS  Google Scholar 

  78. Schleyer PvR, Jiao H, Eikema Hommes NJRv, Malkin VG, Malkina O (1997) J Am Chem Soc 119:12669

    CAS  Google Scholar 

  79. Fowler PW, Steiner E (2000) Mol Phys 98:945

    ADS  Google Scholar 

  80. Corminboeuf C, Heine T, Weber J (2003) Phys Chem Chem Phys 5:246

    CAS  Google Scholar 

  81. Heine T, Schleyer PvR, Corminboeuf C, Seifert G, Reviakine R, Weber J (2003) J Phys Chem A 107:6470

    CAS  Google Scholar 

  82. Fallah-Baghier-Shadaei H, Wannere CS, Corminboeuf C, Puchta R, Schleyer PvR (2006) Org Lett 8:863

    Google Scholar 

  83. Chen Z, Wannere CS, Corminboeuf C, Puchta R, Schleyer PvR (2005) Chem Rev 105:3842

    PubMed  CAS  Google Scholar 

  84. Bultink P, Fias, S, Ponec R (2006) Chem Eur J 12:8813

    Google Scholar 

  85. Jusélius J, Sundholm D (1999) Phys Chem Chem Phys 1:3429

    Google Scholar 

  86. Jusélius J, Sundholm D, Gauss J (2004) J Chem Phys 121:3952

    PubMed  ADS  Google Scholar 

  87. Merino G, Heine T, Seifert G (2004) Chem Eur J 10:4367

    CAS  Google Scholar 

  88. Bader RWF (1991) Chem Rev 91:893

    CAS  Google Scholar 

  89. Becke AD, Edgecombe KE (1990) J Chem Phys 92:5397

    ADS  CAS  Google Scholar 

  90. Chesnut DB, Bartolotti L (2000) Chem Phys 253:1

    CAS  Google Scholar 

  91. Fuster F, Sevin A, Silvi B (2000) J Phys Chem A 104:852

    CAS  Google Scholar 

  92. Dewar MJS (1984) J Am Chem Soc 106:669

    CAS  Google Scholar 

  93. Exner K, Schleyer PvR (2001) J Phys Chem A 105:3407

    CAS  Google Scholar 

  94. Naruse Y, Ma J, Inagaki S (2003) J Phys Chem A 107:2860

    CAS  Google Scholar 

  95. Li Z-H, Moran D, Fan K-N, Schleyer PvR (2005) J Phys Chem A 109:3711

    PubMed  Google Scholar 

  96. Molina JM, El-Bergmi R, Dobado JA, Portal D (2000) J Org Chem 65:8574

    CAS  Google Scholar 

  97. Bachrach SM (1991) J Org Chem 56:2205

    CAS  Google Scholar 

  98. Lee EPF, Nyulászi L, Veszprémi T (1994) J Phys Chem 98:6481

    CAS  Google Scholar 

  99. Göller A, Clark T (2000) J Mol Model 6:133

    Google Scholar 

  100. Huy NHT, Perrier E, Ricard L, Mathey F (2006) Organometallics 25:5176

    CAS  Google Scholar 

  101. See, e.g.: Glukhotsev MN, Laiter S, Pross A (1996) J Phys Chem 100:17801

    Google Scholar 

  102. Deschamps B, Mathey F (1985) Tetrahedron Lett 26:4595

    CAS  Google Scholar 

  103. Eisfeld W, Regitz M (1998) J Org Chem 63:2814

    CAS  Google Scholar 

  104. Simon J, Bergsträsser U, Regitz M, Laali KK (1999) Organometallics 18:817

    CAS  Google Scholar 

  105. Cloke FG, Hitchcock PB, Nixon JF, Vickers DM (2004) Comp Rend Chim 7:931

    CAS  Google Scholar 

  106. Laali KK, Geissler B, Wagner O, Hoffmann J, Armbrust R, Eisfeld W, Regitz M (1994) J Am Chem Soc 116:9407

    CAS  Google Scholar 

  107. Liu X, Ivanova DM, Giblin D, Gross ML, Gaspar PP (2005) Organometallics 24:3125

    CAS  Google Scholar 

  108. Sase S, Kano N, Kawashima T (2006) J Org Chem 71:5448

    PubMed  CAS  Google Scholar 

  109. Ehle M, Wagner O, Bergsträsser U, Regitz, M (1990) Tetrahedron Lett 31:3429

    CAS  Google Scholar 

  110. Campbell BC, Denney DB, Denney DZ, Shih LS (1978) J Chem Soc Chem Commun, p 854

    Google Scholar 

  111. Göller A, Heydt H, Clark T (1996) J Org Chem 61:5840

    Google Scholar 

  112. Castan F, Bacieredo A, Fischer J, Decian A, Commemges G, Bertrand G (1991) J Am Chem Soc 113:8160

    CAS  Google Scholar 

  113. Soleilhavoup M, Canac Y, Polozov AM, Bacieredo A, Bertrand G (1994) J Am Chem Soc 116:6149

    CAS  Google Scholar 

  114. Soleilhavoup M, Bacieredo A, Dahan F, Bertrand G (1994) J Chem Soc Chem Commun, p 337

    Google Scholar 

  115. Bourissou D, Canac Y, Collado MI, Baceiredo A, Bertrand G (1997) J Am Chem Soc 119:9923

    CAS  Google Scholar 

  116. Bourissou D, Bertrand G (1999) Acc Chem Res 32:561

    CAS  Google Scholar 

  117. Moraes LAB, Eberlin MN, Laali K (2001) Organometallics 90:997

    Google Scholar 

  118. Yoshida Z (1973) Top Curr Chem 40:47

    CAS  Google Scholar 

  119. Mathey F (1990) Chem Rev 90:997

    CAS  Google Scholar 

  120. Kato T, Gornitzka H, Baceiredo A, Schoeller WW, Bertrand G (2000) Science 289:754

    PubMed  ADS  CAS  Google Scholar 

  121. Francis MD, Jones C, Junk PC, Roberts LJ (1997) Phosphorus Sulfur Silicon Relat Elem 130:23

    CAS  Google Scholar 

  122. Höltzl T, Szieberth D, Nguyen MT, Veszprémi T (2006) Chem Eur J 12:8044

    Google Scholar 

  123. Höltzl T, Nguyen MT, Veszprémi T (2007) J Mol Struct (THEOCHEM) 811:27

    Google Scholar 

  124. Moran D, Manohoran M, Heine T, Schleyer PvR (2003) Org Lett 5:23

    PubMed  CAS  Google Scholar 

  125. Nyulászi L, Veszprémi T (1996) J Phys Chem 100:6456

    Google Scholar 

  126. Wang ZX, Schleyer PvR (2001) Helv Chim Acta 84:1578

    CAS  Google Scholar 

  127. Mucsi Z, Csizmadia IG (2008) Curr Org Chem 12:83

    CAS  Google Scholar 

  128. Mucsi Z, Viskolcz B, Csi

    Google Scholar 

  129. Bertrand G (1998) Angew Chem Int Ed Engl 37:270

    CAS  Google Scholar 

  130. Krysiak J, Lion C, Baceiredo A, Gornitzka H, Mikolajczik M, Bertrand G (2004) Chem Eur J 10:1982

    CAS  Google Scholar 

  131. Rehaman A, Datta A, Mallajosyula SS, Pati SK (2006) J Chem Theor Comput 2:30

    CAS  Google Scholar 

  132. Bertrand G, Eisfeld W, Nyulászi L, Réau R, Regitz M, Szieberth D (2000) J Chem Soc Perkin Trans II, p 2324

    Google Scholar 

  133. Vedejs E, Marth CF (1990) J Am Chem Soc 112:3905

    CAS  Google Scholar 

  134. Keglevich G, Forintos H, Körtvélyesi T, Toke L (2002) J Chem Soc Perkin Trans I, p 26

    Google Scholar 

  135. Keglevich G, Forintos H, Körtvélyesi T (2004) Curr Org Chem 8:1245

    CAS  Google Scholar 

  136. Kano N, Kikuchi A, Kawashima T (2001) Chem Commun, p 2096

    Google Scholar 

  137. Kawashima T, Iijima T, Kikuchi A, Okazaki R (1999) Phosphorus Sulfur Silicon Relat Elem 144–146:149

    Google Scholar 

  138. Mucsi Z, Körtvélyesi T, Viskolcz B, Csizmadia IG, Novák B, Keglevich G (2007) Eur J Org Chem, p 1759

    Google Scholar 

  139. Niecke E, Fuchs A, Nieger M, Schoeller WW (1995) Angew Chem Int Ed Engl 34:555

    CAS  Google Scholar 

  140. Schmidt O, Fuchs A, Gudat D, Nieger M, Hoffbauer W, Niecke E, Schoeller WW (1998) Angew Chem Int Ed Engl 37:949

    CAS  Google Scholar 

  141. Schoeller WW, Begeman C, Niecke E, Gudat D (2001) J Phys Chem A 105:10736

    Google Scholar 

  142. Niecke E, Fuchs A, Nieger M (1999) Angew Chem Int Ed Engl 38:3028

    PubMed  CAS  Google Scholar 

  143. Sugiyama H, Ito S, Yoshifuji M (2003) Angew Chem Int Ed Engl 42:3802

    PubMed  CAS  Google Scholar 

  144. Niecke E, Fuchs A, Nieger M, Schmidt O, Scoeller WW (1999) Angew Chem Int Ed Engl 38:3031

    PubMed  CAS  Google Scholar 

  145. Sebastian M, Nieger M, Szieberth D, Nyulászi L, Niecke E (2004) Angew Chem Int Ed Engl 43:637

    PubMed  CAS  Google Scholar 

  146. Sekiguchi A, Matsuo T, Watanabe H (2000) J Am Chem Soc 122:5652

    CAS  Google Scholar 

  147. Sekiguchi A, Tanaka M, Matsuo T, Watanabe H (2001) Angew Chem Int Ed Engl 40:1675

    PubMed  CAS  Google Scholar 

  148. Balci M, McKee ML, Schleyer PvR (2000) J Phys Chem A 104:1246

    CAS  Google Scholar 

  149. Kraus F, Aschenbrenner JC, Korber N (2003) Angew Chem Int Ed Engl 42:4030

    PubMed  CAS  Google Scholar 

  150. Kraus F, Hanauer T, Korber N (2006) Inorg Chem 45:1117

    PubMed  CAS  Google Scholar 

  151. Korber N, Reil M (2002) Chem Commun, p 84

    Google Scholar 

  152. Kuznetsov AE, Zhai HJ, Wang LS, Boldyrev AI (2002) Inorg Chem 41:6062

    PubMed  CAS  Google Scholar 

  153. Kraus F, Korber N (2005) Chem Eur J 11:5945

    CAS  Google Scholar 

  154. Jin Q, Jin B, Xu, WG (2004) Chem Phys Lett 396:398

    ADS  CAS  Google Scholar 

  155. Li Z, Zhao C, Chen L (2007) J Mol Struct (THEOCHEM) 810:1

    CAS  Google Scholar 

  156. Francis MD, Hitchcock PB (2003) Organometallics 21:2891

    Google Scholar 

  157. Francis MD, Hitchcock PB (2002) Chem Commun, p 86

    Google Scholar 

  158. Lynam JM, Copsey MC, Green M, Jeffery JC, McGrady JE, Russell CA, Slattery JM, Swain AC (2003) Angew Chem Int Ed Engl 42:2778

    PubMed  CAS  Google Scholar 

  159. Roques C, Maziéres M-R, Majoral JP, Sanchez M, Jaud J (1989) Inorg Chem 28:3931

    CAS  Google Scholar 

  160. Despagnet-Ayoub E, Grubbs RH (2004) J Am Chem Soc 126:10198

    PubMed  CAS  Google Scholar 

  161. Sebstian M, Hoskin A, Nieger M, Nyulászi L, Niecke E (2005) Angew Chem Int Ed Engl 44:1405

    Google Scholar 

  162. Nyulászi L, Schleyer PvR (1999) J Am Chem Soc 121:6872

    Google Scholar 

  163. Bachrach SM (1993) J Org Chem 58:5414

    CAS  Google Scholar 

  164. Dinadayalane TC, Geetha K, Sastry GN (2003) J Phys Chem A 107:5479

    CAS  Google Scholar 

  165. Mathey F (2004) Acc Chem Res 37:9549

    Google Scholar 

  166. Egan W, Tang R, Zon G, Mislow K (1971) J Am Chem Soc 93:6205

    CAS  Google Scholar 

  167. Schäfer W, Schweig A, Mathey F (1976) J Am Chem Soc 98:407

    Google Scholar 

  168. Mattmann E, Simonutti D, Ricard L, Mercier F, Mathey F (2001) J Org Chem 66:755

    PubMed  CAS  Google Scholar 

  169. Mattmann E, Mathey F, Sevin A, Frison G (2002) J Org Chem 67:1208

    PubMed  CAS  Google Scholar 

  170. Chesnut DB, Quin L (2007) Heteroatom Chem 18:754

    CAS  Google Scholar 

  171. Geoffrey F, Cloke N, Hitchcock PB, Nixon JF, Wilson DJ, Nyulászi L, Kárpáti T (2005) J Organomet Chem 690:3983

    CAS  Google Scholar 

  172. Elvers A, Heinemann FW, Wrackmeyer B, Zenneck U (1999) Chem Eur J 5:3143

    CAS  Google Scholar 

  173. Al-Ktaifani MM, Bauer W, Bergstässer U, Breit B, Francis MD, Heinemann FW, Hitchcock PB, Mack A, Nixon JF, Pritzkow H, Regitz M, Zeller M, Zenneck U (2002) Chem Eur J 8:2622

    CAS  Google Scholar 

  174. Heinemann FW, Zeller M, Zenneck U (2004) Organometallics 23:1689

    CAS  Google Scholar 

  175. Quin LD (1996) Phospholes. In: Katritzky AR, Rees CW, Scriven EVF (eds) Comprehensive heterocyclic chemistry II, vol 2. Elsevier, Amsterdam, chap 15

    Google Scholar 

  176. Mucsi Z, Keglevich G (2007) Eur J Org Chem, p 4765

    Google Scholar 

  177. Delare D, Nguyen MT, Vanquickenborne LG (2003) J Phys Chem A 107:838

    Google Scholar 

  178. Chesnut DB (2007) Chem Phys 338:75

    ADS  CAS  Google Scholar 

  179. Padkine A, Cantat T, Deschamps E, Ricard L, Mézailles N, Le Floch P, Geoffroy M (2006) Phys Chem Chem Phys 8:868

    Google Scholar 

  180. Keglevich G, Böcskei Z, Keseru G, Ujszászi K, Quin L (1997) J Am Chem Soc 119:5095

    CAS  Google Scholar 

  181. Cloke FGN, Hitchcock PB, Hunnable P, Nixon JF, Nyulászi L, Niecke E, Thelen V (1998) Angew Chem Int Ed Engl 37:1083

    CAS  Google Scholar 

  182. Ionkin AS, Marshall WJ, Fish BM, Schiffhauer MF, Davidson F, McEwen CN, Keys DE (2007) Organometallics 26:5050

    CAS  Google Scholar 

  183. Nyulászi L, Nixon JF (1999) J Organomet Chem 588:28

    Google Scholar 

  184. Nyulászi L (1995) J Phys Chem 99:586

    Google Scholar 

  185. Jochem G, Nöth H, Schmidpeter A (1996) Chem Ber 129:1083

    CAS  Google Scholar 

  186. Nyulászi L (1996) J Phys Chem 100:6194

    Google Scholar 

  187. Caliman V, Hitchcock PB, Nixon JF (1995) J Chem Soc Chem Commun, p 1661

    Google Scholar 

  188. Caliman V, Hitchcock PB, Nixon JF, Nyulászi L, Sakarya N (1997) Chem Commun, p 1305

    Google Scholar 

  189. Clendening SB, Hitchcock PB, Nixon JF, Nyulászi L (2000) Chem Commun, p 1305

    Google Scholar 

  190. Streubel R, Schiemann U, Jones PG, Grunenberg J, Schiebel H-M, Gudat D (2001) Angew Chem Int Ed Engl 40:2471

    PubMed  CAS  Google Scholar 

  191. Pelzer S, Wichmann K, Wesendrup R, Schwerdtfeger P (2002) J Phys Chem A 106:6387

    CAS  Google Scholar 

  192. Delaere D, Dransfeld A, Nguyen MT, Vanquickenborne LG (2000) J Org Chem 65:2631

    PubMed  CAS  Google Scholar 

  193. Alkorta I, Zborowski K, Elguero J (2006) Struct Chem 17:13

    CAS  Google Scholar 

  194. Pelloni S, Lazzeretti P (2007) Theor Chem Acc 118:89

    CAS  Google Scholar 

  195. Johansson MP, Jusélius J (2005) Lett Org Chem 2:469

    CAS  Google Scholar 

  196. Minkin VI, Glukhovtsev MN, Simkin BYa (1994) Aromaticity and antiaromaticity: electronic and structural aspects. Wiley, New York

    Google Scholar 

  197. Glukhotsev MN, Dransfeld A, Schleyer PvR (1996) J Phys Chem 100:13447

    Google Scholar 

  198. Nyulászi L (1996) Inorg Chem 35:4690

    Google Scholar 

  199. Rocha WR, Duarte LWM, De Almeida WB, Caliman V (2002) J Braz Chem Soc 13:597

    CAS  Google Scholar 

  200. Bansal RK, Gupta N (2004) Product class 20: triphospholes and diphospharsoles. Sci Synth 13:729

    CAS  Google Scholar 

  201. Ozimiński WP, Dobrowolski JCz (2005) Chem Phys 313:123

    Google Scholar 

  202. Wang L, Wang HJ, Dong WB, Ge QY, Lin L (2007) Struct Chem 18:25

    Google Scholar 

  203. Skancke A, Liebman JF (2001) J Mol Struct 567–568:59

    Google Scholar 

  204. Nyulászi L, Szieberth D, Réffy J, Veszprémi T (1998) J Mol Struct (THEOCHEM) 453:91

    CAS  Google Scholar 

  205. Ito S, Sugiyama M, Yoshifuji M (2000) Angew Chem Int Ed Engl 39:2781

    PubMed  CAS  Google Scholar 

  206. Ito S, Miyake H, Yoshifuji M, Höltzl T, Veszprémi T (2005) Chem Eur J 11:5960

    CAS  Google Scholar 

  207. Ekici S, Gudat D, Nieger M, Nyulászi L, Niecke E (2002) Angew Chem Int Ed Engl 41:3368

    Google Scholar 

  208. Yates BY, Bouma WJ, Radom L (1984) J Am Chem Soc 106:5805

    CAS  Google Scholar 

  209. Gudat D (2004) Top Curr Chem 232:175

    CAS  Google Scholar 

  210. Gudat D, Bajorat V, Nieger M (1995) Bull Soc Chim Fr 132:280

    CAS  Google Scholar 

  211. Gudat D, Nieger M, Schrott M (1995) Chem Ber 128:259

    CAS  Google Scholar 

  212. Häp S, Szarvas L, Nieger M, Gudat D (2001) Eur J Inorg Chem 2763

    Google Scholar 

  213. Gudat D, Häp S, Szarvas L, Nieger M (2000) Chem Commun, p 1637

    Google Scholar 

  214. Malar PE (1992) J Org Chem 57:3694

    CAS  Google Scholar 

  215. De Proft F, Fowler PW, Havenith RWA, Schleyer PvR, Van Lier G, Geerling P (2004) Chem Eur J 10:940

    CAS  Google Scholar 

  216. Jin Q, Jin B, Xu WG, Zhu W (2005) J Mol Struct (THEOCHEM) 713:113

    CAS  Google Scholar 

  217. Zhai HJ, Wang LS, Kuznetsov AE, Boldyrev AI (2002) J Phys Chem A 106:5600

    CAS  Google Scholar 

  218. Urnezius E, Brennessel WW, Cramer CJ, Ellis JE, Schleyer PvR (2002) Science 295:832

    ADS  CAS  Google Scholar 

  219. Liu ZZ, Tian W-Q, Feng J-K, Zhang G, Li W-Q (2005) J Phys Chem A 109:5645

    PubMed  CAS  Google Scholar 

  220. Malar EJP (2004) Eur J Inorg Chem 2723

    Google Scholar 

  221. Malar EJP (2005) Theor Chem Acc 114:213

    CAS  Google Scholar 

  222. Bartsch, R, Cloke FGN, Green JC, Matos RM, Nixon JFN, Suffolk RJ, Suter JL, Wilson DJ (2001) J Chem Soc Dalton Trans,p 1013

    Google Scholar 

  223. Zhang L, Hissler M, Bu H-B, Bäuerle P, Lescop C, Réau R (2005) Organometallics 24:5369

    CAS  Google Scholar 

  224. Moser C, Nieger M, Pietschnig R (2006) Organometallics 25:2667

    CAS  Google Scholar 

  225. Francis MD, Hitchcock PB, Nixon JF, Schnöckel H, Steiner J (2002) J Organomet Chem 646:191

    CAS  Google Scholar 

  226. Schnepf A, Stösser G, Carmichael D, Mathey F, Schnöckel H (1999) Angew Chem Int Ed Engl 38:1646

    CAS  Google Scholar 

  227. Callaghan C, Clentsmith GKB, Cloke FGN, Hitchcock PB, Nixon JF, Vickers DM (1999) Organometallics 18:793

    CAS  Google Scholar 

  228. Wann DA, Hinchley SL, Robertson HE, Francis MD, Nixon JF, Rankin DWH (2007) J Organomet Chem 692:1161

    CAS  Google Scholar 

  229. Le Floch P (2006) Coord Chem Rev 250:627

    Google Scholar 

  230. Butts CP, Green M, Hooper TN, Kilby RJ, McGrady JE, Pantazis DA, Russel CA (2008) Chem Commun, p 856

    Google Scholar 

  231. Garcia F, Less RJ, Naseri V, McPartlin M, Rawson JM, Wright DS (2007) Angew Chem Int Ed Engl 46:7827

    PubMed  CAS  Google Scholar 

  232. Panatzis DA, McGrady JE, Lynam JJ, Russel CA, Green M (2004) Dalton Trans, p 2080

    Google Scholar 

  233. Slattery JM, Fish C, Green M, Hooper TN, Jeffery JC, Kilby RJ, Lynam JM, McGrady JE, Pantazis DA, Russel CA, Williams CE (2007) Chem Eur J 13:6967

    CAS  Google Scholar 

  234. Burford N, Ragonga PJ (2002) J Chem Soc Dalton Trans, p 4307

    Google Scholar 

  235. Abrams MB, Scott BL, Baker RT (2000) Organometallics 19:4944

    CAS  Google Scholar 

  236. Hardman NJ, Abrams MB, Pribisko MA, Gilbert TM, Martin RL, Kubas GB, Baker RT (2004) Angew Chem Int Ed Engl 43:1955

    PubMed  CAS  Google Scholar 

  237. Sauers R (1997) Tetrahedron 53:2357

    CAS  Google Scholar 

  238. Carmalt CJ, Lomeli V, McBurnett BG, Cowley AH (1997) J Chem Soc Chem Commun, p 2095

    Google Scholar 

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

    Google Scholar 

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

    CAS  Google Scholar 

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

    PubMed  CAS  Google Scholar 

  242. Gudat D, Haghverdi A, Nieger M (2001) J Organomet Chem 617:383

    Google Scholar 

  243. Gudat D, Haghverdi A, Hoffbauer W (2002) Magn Reson Chem 40:589

    CAS  Google Scholar 

  244. Burford N, Dipchand AI, Royan BW, White PS (1989) Acta Crystallogr 45C:1485

    Google Scholar 

  245. Burford N, Royan BW, Linden A, Cameron TS (1989) Inorg Chem 28:144

    CAS  Google Scholar 

  246. Burford N, Dipchand AI, Royan BW, White PS (1990) Inorg Chem 29:4938

    CAS  Google Scholar 

  247. Benko Z, Gudat D, Nyulászi L (2008) Chem Eur J 14:902

    Google Scholar 

  248. Nguyen MT, McGinn MA, Hegarty AF (1986) Inorg Chem 25:2185

    Google Scholar 

  249. Borissou D, Bertrand G (1999) Adv Organomet Chem 44:175

    Google Scholar 

  250. Dixon DA, Dobbs KD, Arduengo III AJ, Bertrand G (1991) J Am Chem Soc 113:8782

    CAS  Google Scholar 

  251. Igau A, Grütmacher H, Baceiredo A, Bertrand G (1988) J Am Chem Soc 110:6463

    CAS  Google Scholar 

  252. Regitz M (1991) Angew Chem Int Ed Engl 30:674

    Google Scholar 

  253. Regitz M (1996) Angew Chem Int Ed Engl 35:725

    CAS  Google Scholar 

  254. Despagnet E, Gornitzka H, Rozhenko AB, Schoeller WW, Borissou D, Bertrand G (2002) Angew Chem Int Ed Engl 41:2835

    PubMed  CAS  Google Scholar 

  255. Schoeller WW (2004) Eur J Inorg Chem, p 369

    Google Scholar 

  256. Schoeller WW, Eisner D (2004) Inorg Chem 43:2585

    PubMed  CAS  Google Scholar 

  257. Fekete Á, Nyulászi L (2002) J Organomet Chem 643:278

    Google Scholar 

  258. Martin D, Baceiredo A, Gornitzka H, Schoeller WW, Bertrand G (2005) Angew Chem Int Ed Engl 44:1700

    PubMed  CAS  Google Scholar 

  259. Masuda JD, Martin D, Lyon-Saunier C, Baceiredo A, Gornitzka H, Donnadieu B, Bertrand G (2007) Chem Asian J 2:178

    PubMed  CAS  Google Scholar 

  260. Jacobsen H (2006) Dalton Trans, p 2214

    Google Scholar 

  261. Jacobsen H (2005) J Organomet Chem 690:6068

    CAS  Google Scholar 

  262. Cantat T, Mézailles N, Maigrot N, Ricard L, Le Floch P (2004) Chem Commun, p 1274

    Google Scholar 

  263. Fuchs A, Gudat D, Nieger M, Schmidt O, Sebastian M, Nyulászi L, Niecke E (2002) Chem Eur J 8:2188

    CAS  Google Scholar 

  264. Cloke FGN, Hitchcock PB, Nixon JF, Wilson DJ, Tabellion F, Fischbeck U, Preuss F, Regitz M, Nyulászi L (1999) Chem Commun, p 2363

    Google Scholar 

  265. Asmus S, Nyulászi L, Regitz M (2001) J Chem Soc Perkin II, p 1968

    Google Scholar 

  266. Arbeloff-Wilson SE, Hitchcock PB, Nixon JF, Nyulászi L (2002) J Organomet Chem 655:7

    Google Scholar 

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

    Google Scholar 

  268. Bansal RK, Heinicke J (2001) Chem Rev 11:3549

    Google Scholar 

  269. Le Vilain D, Hay C, Deborde V, Toupet L, Réau R (1999) Chem Commun, p 345

    Google Scholar 

  270. Hay C, Fischmeister C, Hissler M, Toupet L, Réau R (2000) Angew Chem Int Ed Engl 39:1812

    PubMed  CAS  Google Scholar 

  271. Baumgartner T (2003) Macromol Symp 196:279

    CAS  Google Scholar 

  272. Baumgartner T, Neumann T Wirges B (2004) Angew Chem Int Ed Engl 43:6197

    PubMed  CAS  Google Scholar 

  273. Hay C, Hissler M, Fischmeister C, Rault-Berthelot J, Toupet L, Nyulászi L, Réau R (2001) Chem Eur J 7:4222

    CAS  Google Scholar 

  274. Baumgartner T, Bergmans W, Kárpáti T, Neumann T, Nieger M, Nyulászi L (2005) Chem Eur J 11:4867

    Google Scholar 

  275. Liu Y-L, Feng J-K, Ren A-M (2007) J Comput Chem 28:2500

    PubMed  CAS  MathSciNet  Google Scholar 

  276. Delare D, Nguyen MT, Vanquickenborne LG (2002) Phys Chem Chem Phys 4:1522

    Google Scholar 

  277. Casado J, Réau R, Navarrete JTL (2006) Chem Eur J 12:3759

    CAS  Google Scholar 

  278. Grundy J, Mathey F (2005) Angew Chem Int Ed Engl 44:1082

    PubMed  CAS  Google Scholar 

  279. Le Floch P (2006) Curr Org Chem 10:3

    Google Scholar 

  280. Kassaee MZ, Jalalimanesh N, Musavi SM (2007) J Mol Struct (THEOCHEM) 816:153

    CAS  Google Scholar 

  281. Salcedo R (2004) J Mol Struct (THEOCHEM) 674:125

    CAS  Google Scholar 

  282. Fernandez I, Frenking G (2007) Faraday Discuss 135:403

    PubMed  CAS  ADS  Google Scholar 

  283. Bachrach SM (2002) J Organomet Chem 643–644:39

    Google Scholar 

  284. Frison G, SevinA, Avarvari N, Mathey F, Le Floch P (1999) J Org Chem 64:5524

    PubMed  CAS  Google Scholar 

  285. Saieswari A, Priyakumar UD, Sastry GN (2003) J Mol Struct (THEOCHEM) 663:145

    CAS  Google Scholar 

  286. Jensen JO (2005) J Mol Struct (THEOCHEM) 729:229

    CAS  Google Scholar 

  287. Hofmann M, Schleyer PvR, Regitz M (1999) Eur J Org Chem 12:3291

    Google Scholar 

  288. Nyulászi L (2005) J Organomet Chem 609–610:2597

    Google Scholar 

  289. Engelberts JJ, Havenith RWA, van Lenthe JH, Jenneskens LW, Fowler PW (2005) Inorg Chem 44:5266

    PubMed  CAS  Google Scholar 

  290. Sakai S (2002) J Phys Chem A 106:10370

    CAS  Google Scholar 

  291. Jemmnis ED, Kiran B (1998) Inorg Chem 37:2110

    Google Scholar 

  292. Dias RHV, Power PP (1987) Angew Chem Int Ed Engl 26:1270

    Google Scholar 

  293. Kaufmann B, Metzler N, Nöth H, PaineRT (1994) Chem Ber 127:825

    CAS  Google Scholar 

  294. Ashe III AJ, Bajkó Z, Carr MD, Kampf JW (2003) Organometallics 22:910

    CAS  Google Scholar 

  295. Müller C, Vogt D (2007) Dalton Trans, p 5505

    Google Scholar 

  296. Elschenbroich C, Six J, Harms K (2006) Chem Commun, p 3429

    Google Scholar 

  297. Elschenbroich C, Nowotny M, Metz B, Massa W, Graulich J, Bieher K, Sauer W (1991) Angew Chem Int Ed Engl 30:547

    Google Scholar 

  298. Arnold PL, Cloke FGN, Khan K, Scott P (1997) J Organomet Chem 77:528

    Google Scholar 

  299. Elschenbroich C, Six J, Harms K (2008) Dalton Trans, p 92

    Google Scholar 

  300. Vijay D, Sastry GN (2006) J Phys Chem A 110:10148

    PubMed  CAS  Google Scholar 

  301. Mézailles N, Ricard L, Mathey F, Le Floch P (1999) Eur J Inorg Chem 2233

    Google Scholar 

  302. Shobe DS (2005) J Phys Chem A 109:9118

    PubMed  CAS  Google Scholar 

  303. Moores A, Cantat T, Ricard L, Mézailles N, Le Floch P (2007) New J Chem 31:1493

    CAS  Google Scholar 

  304. Pham-Tran N-N, Bouchoux G, Delaere D, Nguyen MT (2005) J Phys Chem A 109:2957

    PubMed  CAS  Google Scholar 

  305. Zhang Y, Tham F, Nixon JF, Taylor C, Green JC, Reed CA (2008) Angew Chem Int Ed Engl 120:3861

    Google Scholar 

  306. Moores A, Ricard L, Le Floch P (2003) Angew Chem Int Ed Engl 42:4940

    PubMed  CAS  Google Scholar 

  307. Li W-Q, Tian W-Q, Feng J-K, Liu Z-Z, Ren A-M, Sun C-C, Aoki Y (2007) J Comput Chem 28:1467

    PubMed  CAS  Google Scholar 

  308. Huy NHT, Donnadieau B, Mathey F (2007) Organometallics 26:6497

    CAS  Google Scholar 

  309. Märkl G (1963) Angew Chem Int Ed Engl 2:153

    Google Scholar 

  310. Rzepa HS, Taylor KR (2002) J Chem Soc Perkin Trans II,p 1499

    Google Scholar 

  311. Breza M (2000) J Mol Struct (THEOCHEM) 505:169

    CAS  Google Scholar 

  312. Dewar MJS, Lucken EAC, Whitehead MA (1960) J Chem Soc 2423

    Google Scholar 

  313. Luana V, Pendás M, Costales A, Carriedo GA, Garcia-Alonso FJ (2001) J Phys Chem A 105:5280

    CAS  Google Scholar 

  314. Chaplin AB, Harrison JA, Dyson PJ (2005) Inorg Chem 44:8407

    PubMed  CAS  Google Scholar 

  315. Moores A, Ricard L, Le Floch P, Mézailles N (2003) Organometallics 22:1960

    CAS  Google Scholar 

  316. Renner J, Bergsträsser U, Binger P, Regitz M (2003) Angew Chem Int Ed Engl 42:1863

    PubMed  CAS  Google Scholar 

  317. Li W-Q, Tian W-Q, Feng J-K, Liu Z-Z (2007) Eur J Org Chem, p 1669

    Google Scholar 

  318. Li W-Q, Tian W-Q, Feng J-K, Cui Y-H, Liu Z-Z (2007) J Mol Struct (THEOCHEM) 823:1

    CAS  Google Scholar 

  319. Nyulászi L, Szieberth D, Veszprémi T (1995) J Org Chem 1647

    Google Scholar 

  320. Clendening SB, Hitchcock PB, Lappert MF, Merle PG, Nixon JF, Nyulászi L (2007) Chem Eur J 13:7121

    Google Scholar 

  321. Steinbach J, Binger P, Regitz M (2003) Synthesis 17:2720

    Google Scholar 

  322. Cloke FGN, Hitchcock PB, Nixon JF, Wilson DJ (2000) Organometallics 19:219

    CAS  Google Scholar 

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  1. Department of Inorganic and Analytical Chemistry, Budapest University of Technology and Economics, Szent Gellért tér 4, 1111, Budapest, Hungary

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Nyulászi, L., Benkő, Z. (2008). Aromatic Phosphorus Heterocycles. In: Topics in Heterocyclic Chemistry. Springer, Berlin, Heidelberg. https://doi.org/10.1007/7081_2008_6

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