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Aromaticity of Six-Membered Rings with One Heteroatom

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Book cover Aromaticity in Heterocyclic Compounds

Part of the book series: Topics in Heterocyclic Chemistry ((TOPICS,volume 19))

Abstract

Six-membered rings with one heteroatom are aromatic when there is a continuous conjugation involving six delocalized electrons. The main-group heteroatom from groups 16–13 of the periodic system can be (ordered approximately according to decreasing electronegativity): O+, S+, Se+, Te+, NR+, N+—O−, N, P, PR2, As, Sb, Bi, SiR, GeR, BR−, and GaR−. Among elements that give rise to aromatic metallabenzenes, so far most investigations have concentrated on Os, Ir, Pt, and Rh. Various qualitative and quantitative aspects of aromaticity are reviewed, such as chemical reactivity, molecular geometry, energetics, and magnetic features.

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References

  1. Pozharskii AF, Soldatenkov T, Katritzky AR (1996) Heterocycles in life and society. Wiley, Chichester

    Google Scholar 

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

    Google Scholar 

  3. Balaban AT, Banciu M, Ciorba V (1986) Annulenes, benzo-, hetero-, homo-derivatives and their valence isomers, vol 3. CRC, Boca Raton, p 1

    Google Scholar 

  4. Katritzky AR (1985) Handbook of heterocyclic chemistry. Pergamon, Oxford

    Google Scholar 

  5. Katritzky AR, Rees CW (1984) Comprehensive heterocyclic chemistry, Pergamon, Oxford vols 2, 3

    Google Scholar 

  6. Katritzky AR, Rees CW, Scriven EFV (1984) Comprehensive heterocyclic chemistry II, Elsevier, Amsterdam vol 5

    Google Scholar 

  7. Balaban AT, Oniciu DC, Katritzky AR (2004) Chem Rev 104:2777

    CAS  Google Scholar 

  8. Katritzky AR, Jug K, Oniciu D (2001) Chem Rev 101:1421

    CAS  Google Scholar 

  9. Katritzky AR, Karelson M, Malhotra N (1991) Heterocycles 32:127

    CAS  Google Scholar 

  10. Fernández I, Frenking G (2007) Faraday Discuss 135:403

    Google Scholar 

  11. Frenking G, Krapp A (2006) J Comput Chem 28:15

    Google Scholar 

  12. Balaban AT, Schleyer PvR, Rzepa HS (2005) Chem Rev 105:3436

    CAS  Google Scholar 

  13. Shaik S, Shurki A, Danovich D, Hiberty PC (2001) Chem Rev 101:1501

    CAS  Google Scholar 

  14. Gorelik MV (1990) Russ Chem Rev 59:116

    Google Scholar 

  15. Krygowski TM, Cyrañski MK (2001) Chem Rev 101:1385

    CAS  Google Scholar 

  16. Balaban AT (1980) Pure Appl Chem 52:1409

    CAS  Google Scholar 

  17. King RB (2001) Chem Rev 101:1119

    CAS  Google Scholar 

  18. Chen Z, King RB (2005) Chem Rev 105:3613

    CAS  Google Scholar 

  19. Cyrañski MK (2005) Chem Rev 105:3773

    Google Scholar 

  20. Julg A, François A (1967) Theor Chim Acta 8:249

    CAS  Google Scholar 

  21. Jug KE (1983) J Org Chem 48:1344

    CAS  Google Scholar 

  22. Bird CW (1986) Tetrahedron 42:89

    CAS  Google Scholar 

  23. Bird CW (1993) Tetrahedron 49:8441

    CAS  Google Scholar 

  24. Bird CW (1994) Heterocycles 37:249

    CAS  Google Scholar 

  25. Bird CW (1996) Tetrahedron 52:9945

    CAS  Google Scholar 

  26. Bird CW (1998) Tetrahedron 54:4641

    CAS  Google Scholar 

  27. Kruszewski J, Krygowski TM (1972) Tetrahedron Lett 13:3839

    Google Scholar 

  28. Krygowski TM (1993) J Chem Inf Comput Sci 33:70

    CAS  Google Scholar 

  29. Krygowski TM, Cyrañski M (1995) Tetrahedron 52:1723

    Google Scholar 

  30. Krygowski TM, Cyrañski MK (2004) Phys Chem Chem Phys 6:249

    Google Scholar 

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

    CAS  Google Scholar 

  32. Katritzky AR, Barczynski P, Musumarra G, Pisano D, Szafran (1989) J Am Chem Soc 111:7

    CAS  Google Scholar 

  33. Katritzky AR, Karelson M, Suld S, Krygowski TM, Jug K (1998) J Org Chem 63:5228

    CAS  Google Scholar 

  34. Krygowski TM, Cyrañski MK, Czarnocki Z, Häfelinger G, Katritzky AR (2000) Tetrahedron 56:1783

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  36. Schleyer PvR, Jiao PK (1996) Pure Appl Chem 68:209

    CAS  Google Scholar 

  37. Subramanian G, Schleyer PVR, Jiao H (1996) Angew Chem Int Ed Engl 35:2638

    Google Scholar 

  38. Cyrañski MK, Krygowski TM, Bird CW (1998) Tetrahedron 54:9711

    Google Scholar 

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

    Google Scholar 

  40. Balaban AT, Simon Z (1962) Tetrahedron 18:315

    CAS  Google Scholar 

  41. Saieswari A, Priyakumar UD, Sastry GN (2003) Theochem 663:145

    CAS  Google Scholar 

  42. Priyakumar UD, Sastry GN (2002) J Org Chem 67:271

    CAS  Google Scholar 

  43. Klocker J, Karpfen A, Wolschann P (2003) Theochem 635:141

    CAS  Google Scholar 

  44. Klocker J, Karpfen A, Wolschann P (2003) J Phys Chem A 107:2362

    CAS  Google Scholar 

  45. Torrens F (2004) Mol Divers 8:365

    CAS  Google Scholar 

  46. Balaban AT, Fischer GW, Schroth W (1969) , Pyrylium salts: synthesis. In: Katritzky AR, Boulton AJ (eds) Advances in heterocyclic chemistry, vol 10. Academic, New York, p 241

    Google Scholar 

  47. Balaban AT, Dinculescu A, Dorofeenko GN, Fischer GW, Koblik AV, Mezheritskii VV, Schroth W (1982) Pyrylium salts, Syntheses, reactions, and physical properties, Academic, New York.

    Google Scholar 

  48. Schroth W, Balaban AT (1992) , Pyrylium-Salze. In: Kreher R (ed) Methoden der Organischen Chemie (Houben—Weyl), vol E7b. Thieme, Stuttgart, p 755

    Google Scholar 

  49. Balaban TS, Balaban AT (2003) Pyrylium salts. In: Thomas EJ (ed) Science of synthesis: Houben—Weyl methods of molecular transformations. Thieme, Stuttgart, p 11

    Google Scholar 

  50. Balaban A T (1987) In: Chizov O (ed) Organic synthesis: modern trends. Proceedings 6th IUPAC international symposium on organic synthesis, Moscow, 1986. Blackwell, Oxford, p 263

    Google Scholar 

  51. Balaban AT (1979) In: Mitra RB, Ayyangar NR, Gogte VN, Acheson RN, Cromwell N (eds) New trends in heterocyclic chemistry. Elsevier, Amsterdam, p 79

    Google Scholar 

  52. Collie JN, Tickle T (1899) J Chem Soc 75:710

    CAS  Google Scholar 

  53. Baeyer A, Piccard J (1911) Liebigs Ann Chem 384:208

    Google Scholar 

  54. Miranda MA, García H (1994) Chem Rev 94:1063

    CAS  Google Scholar 

  55. Miranda MA, Izquierdo MA, Pérez-Ruiz R (2003) J Phys Chem A 107:2478

    CAS  Google Scholar 

  56. Law K-Y (1993) Chem Rev 93:449

    CAS  Google Scholar 

  57. Hampel F, Willem D, Schleyer PvR Balaban A T (1992) Tetrahedron 48:6799

    CAS  Google Scholar 

  58. Gard E, Vasilescu A, Mateescu GD, Balaban AT (1967) J Labelled Comp 3:196

    Google Scholar 

  59. Balaban AT (1982) In: Duncan WB, Susan AB (eds) Synthesis and applications of isotopically labelled compounds. Elsevier, Amsterdam, p 237

    Google Scholar 

  60. Uncuta C, Tudose A, Caproiu MT, Stavarache C, Balaban AT (2001) J Chem Res (S), p 170

    Google Scholar 

  61. Uncuta C, Tudose A, Caproiu MT, Stavarache C, Balaban AT (2001) J Chem Res (M), p 523

    Google Scholar 

  62. Uncuta C, Gheorghiu MD, Balaban AT (1987) Tetrahedron Lett 28:3143

    CAS  Google Scholar 

  63. Uncuta C, Gheorghiu MD, Chiraleu F, Plaveti M, Elian M, Balaban AT (1988) Rev Roum Chim 33:719

    CAS  Google Scholar 

  64. Dimroth K (1960) Angew Chem 72:331

    CAS  Google Scholar 

  65. Dimroth K, Neubauer G (1959) Chem Ber 92:2046

    CAS  Google Scholar 

  66. Balaban AT, Mateescu GD, Elian M (1962) Tetrahedron 18:1083

    CAS  Google Scholar 

  67. Balaban AT, Badilescu S, Badilescu II (1984) In: Gupta RR (ed) Physical methods in hetero-cyclic chemistry. Wiley, New York, p 1

    Google Scholar 

  68. Duffield AM, Djerassi C, Balaban AT (1971) Org Mass Spectrom 5:87

    CAS  Google Scholar 

  69. Balaban AT, Bedford GR, Katritzky AR (1964) J Chem Soc 1646

    Google Scholar 

  70. Balaban AT, Wray V, Balaban AT (1971) Org Mass Spectrom 5:87

    Google Scholar 

  71. Balaban AT, Sahini VE, Keplinger E (1960) Tetrahedron 9:163

    CAS  Google Scholar 

  72. Zhou T, Feng S (2002) ChemPhysChem 969

    Google Scholar 

  73. Badilescu S, Balaban AT (1976) Spectrochim Acta 32A:1311

    CAS  Google Scholar 

  74. Badilescu S, Manu I, Balaban A T (1979) Rev Roum Chim 24:947

    CAS  Google Scholar 

  75. Desbene PL, Cherton J-C (1984) Tetrahedron 40:3559

    CAS  Google Scholar 

  76. Kleinpeter E, Spitzner R, Schroth W (1989) Magn Reson Chem 27:713

    CAS  Google Scholar 

  77. Barnes JC, Paton JD, Spitzner R, Schroth W (1990) Tetrahedron 46:2935

    CAS  Google Scholar 

  78. Schroth W (1989) Rev Roum Chim 34:271

    CAS  Google Scholar 

  79. Krygowski TM, Anulewicz R, Pniewska R, Milart P (1991) J Phys Org Chem 4:121

    CAS  Google Scholar 

  80. Turowska-Tyrk I, Krygowski TM, Milart P, Butt G, Topsdom RD (1991) J Mol Struct 245:289

    CAS  Google Scholar 

  81. Turowska-Tyrk I, Krygowski TM, Milart P (1991) J Mol Struct 263:235

    CAS  Google Scholar 

  82. Parreira RLT, Galembeck SE (2006) Theochem 760:59

    CAS  Google Scholar 

  83. Nelson A (2003) In: Thomas EJ (ed) Science of synthesis: Houben—Weyl methods of molecular transformations, vol 14. Thieme, Stuttgart, p 639

    Google Scholar 

  84. Ingall AH (1984) In: Katritzky AR, Rees CW (eds) Comprehensive heterocyclic chemistry, vol 3, part 2B Pergamon, New York, p 885

    Google Scholar 

  85. Ingall AH (1996) In: McKillop A, Katritzky AR, Rees CW, Scriven EFV (eds) Comprehensive heterocyclic chemistryII, vol 5. Pergamon, New York, p 501

    Google Scholar 

  86. Marino JP (1970) Top Sulfur Chem 1:86

    Google Scholar 

  87. Rudorf W-D (2003) In: Thomas EJ (ed) Science of synthesis: Houben— Weyl methods of molecular transformations, vol 14. Thieme, Stuttgart, p 649

    Google Scholar 

  88. Doddi G, Ercolani G (1994) In: Katritzky AR (ed) Advances in heterocyclic chemistry, vol 60. Academic, New York, p 65

    Google Scholar 

  89. Murphy PJ (2003) In: Thomas EJ (ed) Science of synthesis: Houben—Weyl methods of molecular transformations, vol 14. Thieme, Stuttgart, p 817

    Google Scholar 

  90. Honda E, Kataoka T (2004) Curr Org Chem 8:813

    CAS  Google Scholar 

  91. Detty MR, O'Regan MB (1994) Chem Heterocyclic Comp 53:219

    CAS  Google Scholar 

  92. Leonard KA, Nelen MI, Simard TP, Davies SR, Gollnick SO, Oseroff AR, Gibson SL, Hilf R, Chen LB, Detty MR (1999) J Med Chem 42:3953

    CAS  Google Scholar 

  93. Brennan NK, Hall JP, Davies SR, Gollnick SO, Oseroff AR, Gibson SL, Hilf R, Detty MR (2002) J Med Chem 45:5123

    CAS  Google Scholar 

  94. Detty MR, McKelvey JM, Luss HR (1988) Organometallics 7:1131

    CAS  Google Scholar 

  95. Degani I, Fochi R, Vincenzi C (1965) Boll Sci Fac Chim Ind Bologna 23:21, 243

    CAS  Google Scholar 

  96. Yoneda S, Sugimoto T, Yoshida Z (1973) Tetrahedron 29:2009

    CAS  Google Scholar 

  97. Yoneda S, Sugimoto T, Yoshida Z (1972) Tetrahedron 28:5873

    Google Scholar 

  98. Yoshida Z, Sugimoto H, Sugimoto T, Yoneda S (1973) J Org Chem 38:3990

    CAS  Google Scholar 

  99. Yoneda S, Sugimoto T, Tanaka O, Moriya Y, Yoshida Z (1975) Tetrahedron 31:2669

    CAS  Google Scholar 

  100. Pettit R (1960) Tetrahedron Lett 1:11

    Google Scholar 

  101. Degani I, Fochi R, Vincenzi C (1967) Gazz Chim Ital 97:397

    CAS  Google Scholar 

  102. Blustin PH (1979) Chem Phys Lett 63:347

    CAS  Google Scholar 

  103. Radics L, Kardos L (1973) Org Magn Reson 5:251

    CAS  Google Scholar 

  104. Sandor P, Radics L (1980) Org Magn Reson 14:98

    CAS  Google Scholar 

  105. Sandor P, Radics L (1981) Org Magn Reson 16:148

    CAS  Google Scholar 

  106. Palmer MH, Findlay RH (1972) Tetrahedron Lett 13:4165

    Google Scholar 

  107. Palmer MH, Findlay RH, Gaskell AJ (1974) J Chem Soc Perkin Trans II, p 420

    Google Scholar 

  108. Palmer MH, Findlay RH (1974) Tetrahedron Lett 15:253

    Google Scholar 

  109. Palmer MH, Findlay RH, Moyer W, Gaskell AJ (1975) J Chem Soc Perkin Trans II, p 841

    Google Scholar 

  110. Fabian J, Mehlhorn A, Zahradnik R (1968) J Phys Chem 72:3975

    CAS  Google Scholar 

  111. Young TE, Ohnmacht CJ (1967) J Org Chem 32:444

    CAS  Google Scholar 

  112. Salmond WG (1968) Quart Rev 22:253

    CAS  Google Scholar 

  113. Friedman P, Allen LC (1986) Int J Quantum Chem 29:1503

    CAS  Google Scholar 

  114. Afridi AS, Katritzky AR, Ramsden CA (1976) J Chem Soc Chem Commun, p 899

    Google Scholar 

  115. Breda S, Reva I, Lapinski L, Cristiano MLS, Frija L, Fausto R (2006) J Phys Chem A 110:6415

    CAS  Google Scholar 

  116. Suld G, Price CC (1961) J Am Chem Soc 83:1770

    CAS  Google Scholar 

  117. Price CC, Hori M, Parasaran T, Polk M (1963) J Am Chem Soc 85:2278

    CAS  Google Scholar 

  118. Price CC, Follweiler J, Pirelahi H, Siskin M (1971) J Org Chem 36:791

    CAS  Google Scholar 

  119. Price CC, Pirelahi H (1972) J Org Chem 37:1718

    CAS  Google Scholar 

  120. Maryanoff CA, Hayes KS, Mislow K (1977) J Am Chem Soc 99:4412

    CAS  Google Scholar 

  121. Senkler GH, Stackhouse J, Maryanoff BE, Mislow K (1974) J Am Chem Soc 96:17

    Google Scholar 

  122. Maryanoff BE, Stackhouse J, Senkler GH, Mislow K (1975) J Am Chem Soc 97:2718

    CAS  Google Scholar 

  123. Bernardi F , Epiotis ND, Shaik S, Mislow K (1977) Tetrahedron 33:3061

    CAS  Google Scholar 

  124. Senkler GH, Maryanoff BE, Stackhouse J, Andose JD, Mislow K (1975) In: Stirling CJM (ed) Organic sulphur chemistry—structure, mechanism and synthesis. Butterworths, London, p 157

    Google Scholar 

  125. Kassaee MZ, Pirelahi H, Vessally E (2006) Heteroatom Chem 17:376

    CAS  Google Scholar 

  126. Hori M, Kataoka T, Shimizu H, Ohno S, Narita K (1978) Tetrahedron Lett 19:251

    Google Scholar 

  127. Hori M, Kataoka T, Shimizu H, Ohno S, Narita K, Takayanagi H, Ogura H, Iitaka Y (1979) Tetrahedron Lett 20:251

    Google Scholar 

  128. Hori M, Kataoka T, Shimizu H, Matsuo K, Sugimoto A, Ikedo K, Hamada K, Ogura H, Takayanagi H (1987) J Chem Soc Chem Commun, p 385

    Google Scholar 

  129. Shimizu H, Kudo N, Kataoka T , Hori M (1990) Tetrahedron Lett 31:115

    CAS  Google Scholar 

  130. Shimizu H, Kudo N, Kataoka T, Hori M (2001) J Chem Soc Perkin Trans I, p 2269

    Google Scholar 

  131. Weber L (1983) Chem Ber 116:2022

    CAS  Google Scholar 

  132. Weber L, Boese R (1983) Chem Ber 116:514

    CAS  Google Scholar 

  133. Weber L, Wewers D (1983) Chem Ber 116:1327

    CAS  Google Scholar 

  134. Honda E, Iwamura T, Watanabe S, Kataoka T, Muraoka O, Tanabe G (2001) J Chem Soc Perkin Trans I, p 529

    Google Scholar 

  135. Balaban AT (1977) Org Prep Proced Int 9:125

    CAS  Google Scholar 

  136. Balaban AT, Ghiviriga I, Czerwinski EW, De P , Faust R (2004) J Org Chem 69:536

    CAS  Google Scholar 

  137. Johnson SL, Morrison DL (1970) Biochemistry 9:1460

    CAS  Google Scholar 

  138. Johnson SL, Rumon KA (1970) Biochemistry 9:857

    Google Scholar 

  139. Ilies MA, Seitz WA, Johnson BH, Ezell EA, Miller AL, Thompson EB, Balaban AT (2006) J Med Chem 49:3872

    CAS  Google Scholar 

  140. Susan AB, Balaban AT (1969) Rev Roum Chim 14:111

    CAS  Google Scholar 

  141. Katritzky AR (1980) Tetrahedron 36:679

    CAS  Google Scholar 

  142. Katritzky AR (1984) Angew Chem Int Ed Engl 23:420

    Google Scholar 

  143. Camerman A, Jensen LH, Balaban A T (1969) Acta Cryst 25B:2623

    Google Scholar 

  144. Balaban AT, Dinculescu A, Koutrakis HN, Chiraleu F (1979) Tetrahedron Lett 20:437

    Google Scholar 

  145. Balaban AT, Dinculescu A, Iordache F, Chiraleu F, Patrascoiu D (1981) Chem Scripta 18:230

    CAS  Google Scholar 

  146. Elvidge JA, Jackman LM (1961) J Chem Soc, p 859

    Google Scholar 

  147. Krygowski TM, Szatyłowicz H, Zachara JE (2005) J Org Chem 70:8859

    CAS  Google Scholar 

  148. Ośmiałowski B, Kohlemainen E, Nissinen M, Krygowski TM, Gawinecki R (2002) J Org Chem 67:3339

    Google Scholar 

  149. Burnham AK, Lee J, Schmelz TG, Beak P, Flygare WH (1977) J Am Chem Soc 99:1836

    CAS  Google Scholar 

  150. Mçrkl G (1966) Angew Chem Int Ed Engl 5:846

    Google Scholar 

  151. Dimroth K, Hoffmann P (1964) Angew Chem Int Ed Engl 5:384

    Google Scholar 

  152. Dimroth K (1973) Fortschr Chem Forsch 38:1

    Google Scholar 

  153. deKoe P, Bickelhaupt F (1967) Angew Chem Int Ed Engl 6:567

    CAS  Google Scholar 

  154. deKoe P, Bickelhaupt F (1968) Angew Chem Int Ed Engl 7:889

    CAS  Google Scholar 

  155. deKoe P, van Veen R, Bickelhaupt F (1968) Angew Chem Int Ed Engl 7:465

    CAS  Google Scholar 

  156. Vermeer H, Bickelhaupt F (1969) Angew Chem Int Ed Engl 8:992

    CAS  Google Scholar 

  157. Vermeer H, Bickelhaupt F (1970) Tetrahedron Lett 11:3255

    Google Scholar 

  158. Jutzi P (1975) Angew Chem Int Ed Engl 14:232

    Google Scholar 

  159. Jutzi P, Deuchert K (1969) Angew Chem Int Ed Engl 8:991

    CAS  Google Scholar 

  160. Jutzi P (1981) Chem unserer Zeit 15:149

    CAS  Google Scholar 

  161. Ashe III AJ (1971) J Am Chem Soc 93:3923

    Google Scholar 

  162. Ashe III AJ (1971) J Am Chem Soc 93:6691

    Google Scholar 

  163. Mçrkl G (1972) Lect. Heterocycl Chem 1:S-69

    Google Scholar 

  164. Mçrkl G (1982) Chem unserer Zeit 16:139

    Google Scholar 

  165. Ashe III AJ (1978) Acc Chem Res 11:153

    CAS  Google Scholar 

  166. Ashe III AJ (1982) Top Curr Chem 105:125

    CAS  Google Scholar 

  167. Mçrkl G, Lieb F, Merz A (1967) Angew Chem 79:455, 947

    Google Scholar 

  168. Mçrkl G, Fischer DE (1970) Tetrahedron Lett 11:4925

    Google Scholar 

  169. Mçrkl G, Fischer DE, Olbrich H (1970) Tetrahedron Lett 11:645

    Google Scholar 

  170. Mçrkl G, Heier KH (1972) Angew Chem Int Ed Engl 11:1016

    Google Scholar 

  171. Mçrkl G, Heier KH (1972) Angew Chem Int Ed Engl 11:1017

    Google Scholar 

  172. Mçrkl G, Matthes D (1972) Angew Chem Int Ed Engl 11:1019

    Google Scholar 

  173. Mçrkl G, Hauptmann H, Advena J (1972) Angew Chem Int Ed Engl11:441

    Google Scholar 

  174. Mçrkl G, Hauptmann H (1972) Angew Chem Int Ed Engl 11:441

    Google Scholar 

  175. Mçrkl G, Advena J, Hauptmann H (1972) Tetrahedron Lett 13:202, 303

    Google Scholar 

  176. Mçrkl G, Fischer DE (1973) Tetrahedron Lett 14:223

    Google Scholar 

  177. Mçrkl G, Kneidl F (1974) Angew Chem Int Ed Engl 11:667, 668

    Google Scholar 

  178. Mçrkl G, Heier KH (1974) Tetrahedron Lett 15:4369

    Google Scholar 

  179. Mçrkl G, Kellerer H, Kneidl F (1975) Tetrahedron Lett 16:2411

    Google Scholar 

  180. Mçrkl G, Baier H, Heinrich S (1975) Angew Chem Int Ed Engl 14:710

    Google Scholar 

  181. Mçrkl G, Kellerer H, Kneidl F (1976) Tetrahedron Lett 17:665

    Google Scholar 

  182. Mçrkl G (1977) Phosphorus Sulfur, p 77

    Google Scholar 

  183. Mçrkl G, Liebl R (1977) Angew Chem Int Ed Engl 16:637

    Google Scholar 

  184. Mçrkl G, Rampal JB (1977) Tetrahedron Lett 18:3449

    Google Scholar 

  185. Mçrkl G, Rampal JB (1977) Tetrahedron Lett 19:1175

    Google Scholar 

  186. Mçrkl G, Liebl R (1980) Liebigs Ann Chem, p 2095

    Google Scholar 

  187. Mçrkl G, Liebl R, Baier H (1981) Liebigs Ann Chem, p 1610

    Google Scholar 

  188. Batich C, Heilbronner E, Hornung V, Ashe III AJ, Clark DT, Cobley UT, Kilcast D, Scanlan D (1973) J Am Chem Soc 95:928

    CAS  Google Scholar 

  189. Ashe III AJ, Gordon MD (1972) J Am Chem Soc 94:7596

    CAS  Google Scholar 

  190. Kuczkowski RL, Ashe III AJ (1972) J Mol Spectrosc 42:457

    CAS  Google Scholar 

  191. Ashe III AJ, Chan W-T (1975) Tetrahedron Lett 16:2749

    Google Scholar 

  192. Ashe III AJ, Chan W-T, Perozzi E (1975) Tetrahedron Lett 16:1083

    Google Scholar 

  193. Ashe III AJ (1976) Tetrahedron Lett 17:415

    Google Scholar 

  194. Ashe III AJ, Sharp RR, Tolan JW (1976) J Am Chem Soc 98:5451

    CAS  Google Scholar 

  195. Ashe III AJ, Smith TW (1976) J Am Chem Soc 98:7861

    CAS  Google Scholar 

  196. Ashe III AJ, Smith TW (1977) Tetrahedron Lett 18:407

    Google Scholar 

  197. Ashe III AJ, Chan W-T, Smith TW (1978) Tetrahedron Lett 19:2537

    Google Scholar 

  198. Fong GD, Kuczkowski RL, Ashe III AJ (1978) J Mol Spectrosc 70:197

    CAS  Google Scholar 

  199. Ashe III AJ, Chan W-T (1979) J Org Chem 44:1409

    CAS  Google Scholar 

  200. Ashe III AJ, Bahl MK, Bomben KD, Chan W-T, Gimzewski JK, Sitton PG, Thomas TD (1979) J Am Chem Soc 101:1764

    Google Scholar 

  201. Wong TC, Ferguson MG, Ashe III AJ (1979) J Mol Struct 52:231

    CAS  Google Scholar 

  202. Ashe III AJ, Chan W-T (1980) J Org Chem 45:2016

    CAS  Google Scholar 

  203. Ashe III AJ, Chan W-T, Smith TW, Taba KM (1981) J Org Chem 46:881

    CAS  Google Scholar 

  204. Burrow PD, Ashe III AJ, Bellville DJ, Jordan KD (1982) J Am Chem Soc 104:425

    CAS  Google Scholar 

  205. Ashe III AJ, Diephouse TR, El_Sheikh MY (1982) J Am Chem Soc 104:5693

    CAS  Google Scholar 

  206. Ashe III AJ, Jones GL, Miller FA (1982) J Mol Struct 78:169

    CAS  Google Scholar 

  207. Ashe III AJ, Abu-Orabi ST (1983) J Org Chem 48:767

    CAS  Google Scholar 

  208. Ashe III AJ, Ludwig EG (1986) J Organometal Chem 303:197

    CAS  Google Scholar 

  209. Ludwig EG, Ashe III AJ (1986) J Organometal Chem 308:289

    Google Scholar 

  210. Ashe III AJ, Mahmoud S, Eischenbroisch C, Wünsch M (1987) Angew Chem Int Ed Engl 26:229

    Google Scholar 

  211. Waluk J, Klein H-P, Ashe III AJ, Michl J (1989) Organometallics 8:2804

    CAS  Google Scholar 

  212. Hodges RV, Beauchamp JL, Ashe III AJ, Chan W-T (1989) Organometallics 4:457

    Google Scholar 

  213. Lohr LL, Ashe III AJ (1993) Organometallics 12:343

    CAS  Google Scholar 

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

    Google Scholar 

  215. Wong Z, Schleyer PvR (2001) Helv Chim Acta 84:1578

    Google Scholar 

  216. Kieselack P, Helland C, Dimroth K (1975) Chem Ber 108:3656

    CAS  Google Scholar 

  217. Dimroth K (1982) Acc Chem Res 15:58

    CAS  Google Scholar 

  218. Wakita K, Tokitoh N, Okazaki R, Nagase S (2000) Angew Chem Int Ed Engl 39:634

    CAS  Google Scholar 

  219. Wakita K, Tokitoh N, Okazaki R, Takagi N, Nagase S (2000) J Am Chem Soc 122:5648

    CAS  Google Scholar 

  220. Nakata N, Takeda N, Tokitoh N (2002) J Am Chem Soc 124:6914

    CAS  Google Scholar 

  221. Tokitoh N (2004) Acc Chem Res 37:86

    CAS  Google Scholar 

  222. Barton TJ, Banasiak DS (1977) J Am Chem Soc 99:5199

    CAS  Google Scholar 

  223. Barton TJ, Burns GT (1978) J Am Chem Soc 100:5246

    CAS  Google Scholar 

  224. Bock H, Bowling RA, Solouki B, Barton TJ, Burns GT (1980) J Am Chem Soc 102:429

    CAS  Google Scholar 

  225. Kreil CL, Chapman OL, Burns GT Barton TJ (1980) J Am Chem Soc 102:841

    CAS  Google Scholar 

  226. Barton TJ, Vuper M (1981) J Am Chem Soc 103:6788

    CAS  Google Scholar 

  227. Maier G, Mihm G, Reisenauer HP (1980) Angew Chem Int Ed Engl 19:52

    Google Scholar 

  228. Maier G, Mihm G, Reisenauer HP (1981) Angew Chem Int Ed Engl 20:597

    Google Scholar 

  229. Reisenauer HP, Mihm G, Maier G (1982) Angew Chem Int Ed Engl 21:854

    Google Scholar 

  230. Maier G, Mihm G, Reisenauer HP (1982) Chem Ber 115:801

    CAS  Google Scholar 

  231. Maier G, Mihm G, Reisenauer HP (1984) Chem Ber 117:2351

    CAS  Google Scholar 

  232. Maier G, Mihm G, Reisenauer HP, Littman D (1984) Chem Ber 117:2369

    CAS  Google Scholar 

  233. Bock H, Rosmus P , Solouki B, Maier G (1984) J Organomet Chem 271:145

    CAS  Google Scholar 

  234. Maier G (1986) Pure Appl Chem 58:95

    CAS  Google Scholar 

  235. Jutzi P, Meyer M, Reisenauer HP, Maier G (1989) Chem Ber 122:1227

    CAS  Google Scholar 

  236. Mçrkl G, Hofmeister P (1979) Angew Chem Int Ed Engl 18:789

    Google Scholar 

  237. Mçrkl G, Schlosser W (1988) Angew Chem Int Ed Engl 27:963

    Google Scholar 

  238. Mçrkl G, Rudnick D (1980) Tetrahedron Lett 21:1405

    Google Scholar 

  239. Mçrkl G, Rudnick D, Schulz R, Schweig A (1982) Angew Chem Int Ed Engl 21:221

    Google Scholar 

  240. Mçrkl G, Rudnick D (1980) Tetrahedrom Lett 21:1405

    Google Scholar 

  241. Chandrasekhar J, Schleyer PvR, Baumgçrtner ROW, Reetz MT (1983) J Org Chem 48:3453

    CAS  Google Scholar 

  242. Dhevi DM, Priyakumr UD, Sastry GN (2003) J Org Chem 68:1168

    CAS  Google Scholar 

  243. Schlegel HB, Coleman B, Jones M (1978) J Am Chem Soc 100:6499

    CAS  Google Scholar 

  244. Baldridge KK, Gordon MS (1988) Organometallics 7:144

    CAS  Google Scholar 

  245. Baldridge KK, Gordon MS (1988) J Am Chem Soc 110:4204

    CAS  Google Scholar 

  246. Baldridge KK, Uzan O, Martin JML (2000) Organometallics 19:1477

    CAS  Google Scholar 

  247. El-Nahas AM, Johansson M, Ottoson H (2003) Organometallics 22:5556

    Google Scholar 

  248. Dewar MJS, Pettit R (1955) Chem Ind (London), p 199

    Google Scholar 

  249. Dewar MJS, Pettit R (1956) J Chem Soc, p 2021

    Google Scholar 

  250. Dewar MJS, Pettit R (1956) J Chem Soc, p 2026

    Google Scholar 

  251. Boese R, Finke N, Henkelman J, Maier G, Paetzold P, Reisenauer HP, Schmid G (1985) Chem Ber 118:1644

    CAS  Google Scholar 

  252. Sullivan SA, Sandford HF, Beauchamp JL Ashe III AJ (1978) J Am Chem Soc 100:3737

    CAS  Google Scholar 

  253. Ashe III AJ, Shu P (1971) J Am Chem Soc 93:1804

    CAS  Google Scholar 

  254. Herberich GE, Greiss G, Heil HF (1970) Angew Chem Int Ed Engl 9:805

    CAS  Google Scholar 

  255. Herberich GE, Becker HJ (1973) Angew Chem Int Ed Engl 12:764

    Google Scholar 

  256. Herberich GE, Ohst H (1986) Adv Organomet Chem 25:199

    CAS  Google Scholar 

  257. Herberich GE, Schmidt B, Englert U, Wagner T (1993) Organometallics 12:2891

    CAS  Google Scholar 

  258. Herberich GE, Schmidt B, Englert U (1995) Organometallics 14:471

    CAS  Google Scholar 

  259. Huttner G, Gartzke W (1974) Chem Ber 107:3786

    CAS  Google Scholar 

  260. Huttner G, Krieg B, Gartzke W (1972) Chem Ber 105:3424

    CAS  Google Scholar 

  261. Hoic DA, Davis WM, Fu GC (1995) J Am Chem Soc 117:8480

    CAS  Google Scholar 

  262. Qiao S, Hoic DA, Fu GC (1996) J Am Chem Soc118:6329

    CAS  Google Scholar 

  263. Ashe III AJ, Meyers E, Shu P, Lehmann TV, Bastide J (1975) J Am Chem Soc 97:6865

    CAS  Google Scholar 

  264. Ashe III AJ, Kampf JW, Müller C, Schneider M (1975) Organometallics 15:387

    Google Scholar 

  265. Ashe III AJ, Butler W, Sandford HF (1979) J Am Chem Soc 101:7065

    Google Scholar 

  266. Ashe III AJ, Drone FJ, Kausch CM, Kroker J, Al-Taweel SM (1975) Pure Appl Chem 62:513

    Google Scholar 

  267. Ashe III AJ, Al-Ahmad S, Fang X (1999) J Organometal Chem 581:99

    Google Scholar 

  268. Wood TK, Piers WE, Keay BA, Parvez M (2006) Org Lett8:2875

    CAS  Google Scholar 

  269. Karadkov PB, Ellis M, Gerratt J, Cooper DL, Raimondi M (1997) Int J Quantum Chem 63:441

    Google Scholar 

  270. Schulman JM, Disch RL (1989) Organometallics 8:733

    CAS  Google Scholar 

  271. Ashe III AJ, Al-Ahmad S, Kampf JW (1995) Angew Chem Int Ed Engl 34:1357

    CAS  Google Scholar 

  272. Hoffmann R (1982) Angew Chem Int Ed Engl 21:711

    Google Scholar 

  273. Elian M, Chen MM-L, Mingos DMP, Hoffmann R (1976) Inorg Chem 15:1148

    CAS  Google Scholar 

  274. Thorn DR, Hoffmann R (1979) Nouv J Chem 3:39

    CAS  Google Scholar 

  275. Elliott GP, Roper WR, Waters JM (1982) J Chem Soc Chem Commun, p 811

    Google Scholar 

  276. Elliott GP, McAuley NM, Roper WR (1989) Inorg Synth 26:184

    CAS  Google Scholar 

  277. Grabowski NA, Hughes RP, Jaynes BS, Rheingold AL (1986) J Chem Soc Chem Commun, p 1694

    Google Scholar 

  278. Egan JW Jr, Hughes RP, Rheingold AL (1987) Organometallics 16:1103

    Google Scholar 

  279. Bleeke JR, Xie Y-F, Peng W-J, Chiang M (1989) J Am Chem Soc 111:4118

    CAS  Google Scholar 

  280. Bleeke JR, Behm R, Beatty AM (1997) Organometallics 16:1103

    CAS  Google Scholar 

  281. Bleeke JR, Hinkle PV, Shokeen M, Rath NP (2004) Organometallics 23:4130

    Google Scholar 

  282. Wen TB, Zhou ZY, Jia G (2001) Angew Chem Int Ed Engl 40:1951

    CAS  Google Scholar 

  283. Hung WY, Zhu J, Wen TB, Yu KP, Sung HHY, Williams ID, Lin Z, Jia G (2006) J Am Chem Soc 128:13742

    CAS  Google Scholar 

  284. Zhu J, Jia G, Lin Z (2007) Organometallics 26:1986

    CAS  Google Scholar 

  285. Bleeke JR, Behm R (1997) J Am Chem Soc 119:8503

    CAS  Google Scholar 

  286. Yang J, Jones WM, Dixon JK, Allison NT (1995) J Am Chem Soc 117:9776

    CAS  Google Scholar 

  287. Paneque M, Posadas CM, Poveda ML, Rendóm N, Salazar V, Onate E, Mereiter K (2003) J Am Chem Soc 125:9898

    CAS  Google Scholar 

  288. Landorf CW, Haley MM (2006) Angew Chem Int Ed Engl 45:3914

    CAS  Google Scholar 

  289. Bleeke JR (1991) Acc Chem Res 24:271

    CAS  Google Scholar 

  290. Bleeke JR (2001) Chem Rev 101:1205

    CAS  Google Scholar 

  291. Wright L J (2006) Dalton Trans, p 1821

    Google Scholar 

  292. Fernandez I, Frenking G (2007) Chem Eur J 13:5873

    CAS  Google Scholar 

  293. Bleeke JR, Behm R, Xie Y-F, Peng W-J, Chiang MY, Robinson KD, Beatty AM (1997) Organometallics 16:606

    CAS  Google Scholar 

  294. Hughes RP, Trujillo HA, Rheingold AL (1993) J Am Chem Soc 115:1583

    CAS  Google Scholar 

  295. Hughes RP, Trujillo HA, Egan JW Jr, Rheingold AL (2000) J Am Chem Soc 122:2261

    CAS  Google Scholar 

  296. Iron MA, Martin JML, van der Boom ME (2003) J Am Chem Soc 125:13020

    CAS  Google Scholar 

  297. Roper WR (2001) Angew Chem Int Ed Engl 40:2440

    CAS  Google Scholar 

  298. Barrio P, Esteruelas Oñate E (2004) J Am Chem Soc 126:1946

    CAS  Google Scholar 

  299. Iron MA, Lucassen ACB, Cohen H, ven der Boom ME, Martin JML (2004) J Am Chem Soc 126:11699

    CAS  Google Scholar 

  300. Zhang H, Feng L, Gong L, Wu L, He G, Wen T, Yang F, Xia H (2007) Organometallics 26:2705

    CAS  Google Scholar 

  301. Liu SH, Ng WS, Ghu HS, Wen TB, Xia H, Zhou ZY, Lau CP, Jia G (2002) Angew Chem Int Ed Engl 41:1589

    CAS  Google Scholar 

  302. Effertz U, Englert U, Podewils F, Salzer A, Wagner T, Kaupp M (2003) Organometallics 22:264

    CAS  Google Scholar 

  303. Landorf CW, Jacob V, Weakley TJR, Haley MM (2004) Organometallics 23:1174

    CAS  Google Scholar 

  304. Jacob V, Weakley TJR, Haley MM (2002) Angew Chem Int Ed Engl 41:3470

    CAS  Google Scholar 

  305. Gilbertson RD, Lau TLS, Lanza S, Wu H, Weakley TJR, Haley MH (2003) Organometallics 22:3279

    CAS  Google Scholar 

  306. Xia H, He G, Zhang H, Wen TB, Sung HHY, Williams ID, Jia G (2004) J Am Chem Soc 126:6862

    CAS  Google Scholar 

  307. Wu H, Lanza S, Weakley TJR, Haley MM (2002) Organometallics 21:2824

    CAS  Google Scholar 

  308. Wu H, Weakley TJR, Haley MM (2002) Organometallics21:4320

    CAS  Google Scholar 

  309. Balaban AT, Banciu M, Ciorba V (1986) Annulenes, benzo-, hetero-, homo-derivatives and their valence isomers. CRC, Boca Raton vol 1

    Google Scholar 

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  1. Texas A&M University at Galveston, 5007 Avenue U, Galveston, TX, 77551, USA

    A.T. Balaban

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  1. Department of Chemistry, University of Warsaw, ul. Pasteura 1, Warszawa, 02-093, Poland

    Tadeusz M. Krygowski  & Michał K. Cyrański  & 

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Balaban, A. (2009). Aromaticity of Six-Membered Rings with One Heteroatom. In: Krygowski, T.M., Cyrański, M.K. (eds) Aromaticity in Heterocyclic Compounds. Topics in Heterocyclic Chemistry, vol 19. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-540-68343-8_5

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