Advertisement

Polycyclic anions: From doubly to highly charged π-conjugated systems

  • Mordecai Rabinovitz
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 146)

Keywords

Metal Reduction Aromatic Character Lithium Salt Negative Charge Density Bond Length Alternation 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

10 References

  1. 1. (a)
    Cram DJ 1965 Fundamentals of Carbanion Chemistry, Academic Press, New YorkGoogle Scholar
  2. 1. (b)
    Joner JR 1973 The Ionization of Carbon Acids, Academic Press, New YorkGoogle Scholar
  3. 1. (c)
    Kaiser EM, Slocum DW 1973 McManus SP (Ed) in: Organic Reactive Intermediates, Academic Press, New York, Chapter 5Google Scholar
  4. 1. (d)
    Ebel HF 1969 Die Acidität des CH-Sauren, George Thieme Verlag, StuttgartGoogle Scholar
  5. 2. (a)
    Szwarc M 1974 Ions and Ion Pairs in Organic Reactions, Wiley Interscience, New York 1972. Vol. 2Google Scholar
  6. 2. (b)
    Szwarc M (1968) in: Streitwieser A, Taft RW (eds) Progress in Physical Organic Chemistry, Interscience Publishers, New York, Vol. 6, pp. 323Google Scholar
  7. 2. (c)
    Szwarc M (1969) Acc. Chem. Res. 2: 87Google Scholar
  8. 2. (d)
    Szwarc M (1972) ibid. 5: 169Google Scholar
  9. 3. (a)
    Buncel E 1975 Carbanions: Mechanistic and Isotropic Aspects, Elsevier, AmsterdamGoogle Scholar
  10. 3. (b)
    Buncel E, Durst T 1981 Comprehensive Carbanion Chemistry, Elsevier, New YorkGoogle Scholar
  11. 4.
    Thiele J (1900); Ber. 33: 660; (1901) 34: 68Google Scholar
  12. 5. (a)
    Schlenk W, Appenrodt J, Michael A, Thal A (1914) Chem. Ber. 47: 473Google Scholar
  13. 5. (b)
    Schlenk W, Bergmann E (1928) Liebigs Ann. Chem. 463: 1Google Scholar
  14. 6.
    Cannon RD 1981 Electron Transfer Reactions, Butterworth, LondonGoogle Scholar
  15. 7.
    Scott ND, Walker JF, Hansley VL (1936) J. Am. Chem. Soc. 58: 2442Google Scholar
  16. 8.
    Müllen K (1984) Chem. Rev. 84: 603Google Scholar
  17. 9.
    Streitwieser A Jr, Suzuki S (1961) Tetrahedron 16: 153Google Scholar
  18. 10.
    Lawler RG, Ristagno CV (1969) J. Am. Chem. Soc. 91: 1534Google Scholar
  19. 11. (a)
    Ristagno CV, Lawler RG (1973) Tetrahedron Lett. 159Google Scholar
  20. 11. (b)
    Müllen K (1976) Helv. Chim. Acta 59: 1357Google Scholar
  21. 12.
    Gerson F, Müllen K, Vogel E (1971) Angew. Chem. Int. Ed. Engl. 10: 920Google Scholar
  22. 13.
    Paul DE, Lipkin D, Weissman SI (1956) J. Am. Chem. Soc. 78: 116Google Scholar
  23. 14.
    Jensen BS, Parker VD (1975) ibid. 97: 5211Google Scholar
  24. 15.
    Jensen BS, Parker VD (1974) J.C.S. Chem. Commun. 367Google Scholar
  25. 16.
    Bard AJ, Faulkner L 1980 Electrochemical Methods, Fundamentals and Applications, Wiley, New YorkGoogle Scholar
  26. 17. (a)
    Heinze J (1984) Angew. Chem. Int. Ed. Engl. 23: 831Google Scholar
  27. 17. (b)
    Mortensen J, Heinze J (1985) Tetrahedron Lett. 26: 415Google Scholar
  28. 18. (a)
    Hoijtink GJ, Zandstra PJ (1960) Mol. Phys. 3: 371Google Scholar
  29. 18. (b)
    Buschow KHJ, Hoijtink GJ (1964) J. Chem. Phys. 40: 2501Google Scholar
  30. 18. (c)
    Eleoranta J, Linschitz H (1963) ibid. 38: 2214Google Scholar
  31. 19.
    Frim R, Rabinovitz M, Muszkat KA (1987) J.C.S. Chem. Commun., in the pressGoogle Scholar
  32. 20.
    Streitwieser A Jr 1961 MO Theory for Organic Chemists, J. Wiley, New YorkGoogle Scholar
  33. 21.
    Klein J (1983) Tetrahedron Report No. 152, Tetrahedron 39: 2733 and references cited thereinGoogle Scholar
  34. 22.
    Cohen Y, Klein J, Rabinovitz M (1986) J.C.S. Chem. Commun. 1071Google Scholar
  35. 23. (a)
    Bates RB, Gosselink DW, Kaczynski CJ (1969) Tetrahedron Lett. 205Google Scholar
  36. 23. (b)
    Klein J, Brenner S (1969) J. Am. Chem. Soc. 91: 3094Google Scholar
  37. 23. (c)
    Klein J, Brenner S (1970) Tetrahedron 26: 5807Google Scholar
  38. 23. (d)
    Klein J, Medlik A (1973) J.C.S. Chem. Commun. 275Google Scholar
  39. 24. (a)
    Heiszwolf GJ, van Drunen JAA, Kloosterziel H (1969) Recl. Trav. Chim. Pays Bas 88: 1377Google Scholar
  40. 24. (b)
    Kloosterziel H, van Drunen JAA (1970) ibid. 89: 270Google Scholar
  41. 24. (c)
    Streitwieser A, Jr, Chang CJ, Reuben DM (1972) J. Am. Chem. Soc. 94: 5730Google Scholar
  42. 24. (d)
    Streitwieser A, Jr, Murdoch JR, Hafelinger G, Chang CJ (1973) ibid. 95: 4248Google Scholar
  43. 24. (e)
    Lochmann L, Pospisil J, Lim D (1967) Tetrahedron Lett 257Google Scholar
  44. 24. (f)
    Schlosser M, Hartmann J (1973) Angew. Chem. 85: 544Google Scholar
  45. 25.
    Harvey RG, Cho H (1974) J. Am. Chem. Soc. 96: 2434Google Scholar
  46. 26. (a)
    Young RN (1979) Progress Nucl. Mag. Reson. Spectrosc. 12: 261Google Scholar
  47. 26. (b)
    O'Brian DH (1980) in: Comprehensive Carbanion Chemistry, Buncel E, Durst T (Eds), Elsevier Amsterdam Part A, pp. 271Google Scholar
  48. 27. (a)
    O'Brian DH, Hart AJ (1975) J. Am. Chem. Soc. 97: 4410Google Scholar
  49. 27. (b)
    O'Brian DH, Russel CR, Hart AJ (1979) ibid. 101: 633Google Scholar
  50. 28.
    Günther H (1980) NMR Spectroscopy, J. Wiley Chapter 6, pp. 67–70Google Scholar
  51. 29. (a)
    Fraenkel G, Carter RE, MacLean A, Richards JH (1960) J. Am. Chem. Soc. 82: 5846Google Scholar
  52. 29. (b)
    Farnum DG (1975) Gold V, Bethel D (Eds) Adv. Phys. Org. Chem. Vol. 11, p. 123, Academic Press, LondonGoogle Scholar
  53. 30.
    Schaefer R, Schneider WG (1963) Can. J. Chem. 41: 966Google Scholar
  54. 31.
    Spiesecke H, Schneider WG (1961) Tetrahedron Lett. 468Google Scholar
  55. 32. (a)
    Forsyth DH, Spear RJ, Olah GA (1976) J. Am. Chem. Soc. 98: 2512Google Scholar
  56. 33.
    Strub H, Beeler AJ, Grant D, Michl J, Cutts PW, Zilm KW (1983) ibid. 105: 3333Google Scholar
  57. 34.
    Linder M, Hohemner A, Ernst RR (1974) J. Mag. Res. 35: 379Google Scholar
  58. 35.
    Minsky A, Meyer AY, Rabinovitz M (1982) Tetrahedron Lett. 23: 5351Google Scholar
  59. 36.
    Minsky A, Meyer AY, Rabinovitz M (1985) Tetrahedron 41: 785Google Scholar
  60. 37. (a)
    Minsky A, Meyer AY, Rabinovitz M (1983) Angew. Chem. Int. Ed. Engl. 22: 45Google Scholar
  61. 37. (b)
    Minsky A, Meyer AY, Poupko R, Rabinovitz M (1983) J. Am. Chem. Soc. 105: 2164Google Scholar
  62. 37. (c)
    Cohen Y, Rabinovitz M, to be publishedGoogle Scholar
  63. 38.
    Breslow R (1973) Acc. Chem. Res. 6: 393Google Scholar
  64. 39. (a)
    Mallion RB (1973) Molec. Physics 25: 1415Google Scholar
  65. 39. (b)
    Haigh CW, Mallion EB (1980) Progress, Nucl. Mag. Res. 13: 303; see ref. 50Google Scholar
  66. 40.
    Karplus M, Pople JA (1963) J. Chem. Phys. 38: 2803Google Scholar
  67. 41.
    Eliasson B, Edlund U, Müllen K (1986) J. Chem. Soc., Perkin II, 937Google Scholar
  68. 42. (a)
    Haddon RC, Haddon VR, Jackman LM (1970) Fortschr. Chem. Forsch. 16: 103Google Scholar
  69. 42. (b)
    Musher JI (1965) J. Chem. Phys. 43: 3081Google Scholar
  70. 43. (a)
    Pople JA, Schneider WG, Bernstein HJ 1959 High Resolution Nuclear Magnetic Resonance, McGraw-Hill, New YorkGoogle Scholar
  71. 43. (b)
    Pople Ja, Untch KG (1966) J. Am. Chem. Soc. 88: 4811Google Scholar
  72. 44. (a)
    Günther H (1980) NMR Spectroscopy, J. Wiley, N.Y., p. 77–79Google Scholar
  73. 44. (b)
    Benn R, Günther H (1983) Angew. Chem. Int. Ed. Engl. 22: 350Google Scholar
  74. 45. (a)
    Emsley JW, Feeney J, Sutcliffe LH 1966 High Resolution NMR Spectroscopy, Pergamon Press, OxfordGoogle Scholar
  75. 45. (b)
    Jackman LM, Sondheimer F, Amiel Y, Ben Efraim DA, Gaony Y, Wolovsky R, Bothner-By AA (1962) J. Am. Chem. Soc. 84: 4307Google Scholar
  76. 46.
    Pawliczek JB, Gunther H (1970) Tetrahedron 26: 1755Google Scholar
  77. 47.
    Sondheimer F, Calder IC, Elix JA, Gaoni Y, Garratt PJ, Grohmann K, de Maio G, Sargent MV, Wolovsky R (1967) Chem. Soc. Spec. Publ. No. 21, 75Google Scholar
  78. 48.
    Sondheimer F (1972) Acc. Chem. Res. 5: 81Google Scholar
  79. 49. (a)
    Boeckelheide V (1973) in: Nozoe T (Ed) Topics in Nonbenzenoid Aromatic Chemistry, Hirkawa, TokyoGoogle Scholar
  80. 49. (b)
    Boeckelheide V (1975) Pure Appl. Chem. 44: 751Google Scholar
  81. 50.
    Mallion RB (1980) ibid. 52: 1541Google Scholar
  82. 51. (a)
    Vogel E (1967) Chem. Soc. Spec. Publ. No. 21, 113Google Scholar
  83. 51. (b)
    Vogel E (1971) Pure Appl. Chem. 28: 355Google Scholar
  84. 51. (c)
    Vogel E (1980) Israel J. Chem. 20: 215Google Scholar
  85. 52. (a)
    Schröder G (1975) Pure Appl. Chem. 44: 925Google Scholar
  86. 52. (b)
    Abraham R (1961) J. Mol. Phys. 4: 145Google Scholar
  87. 53. (a)
    Carrington A, McLachlan AD 1967 Introduction to Magnetic Resonance, Harper and Row London, p. 57Google Scholar
  88. 53. (b)
    Ramsey NF (1950) Phys. Rev. 78: 699Google Scholar
  89. 53. (c)
    Karplus M, Pople JA (1963) J. Chem. Phys. 38: 2802Google Scholar
  90. 54. (a)
    Gerson F 1970 High Resolution ESR Spectroscopy, Wiley, New YorkGoogle Scholar
  91. 54. (b)
    Wert JE, Bolton JR 1972 ESR Elementary Theory and Practical Applications, McGraw-Hill, New YorkGoogle Scholar
  92. 55.
    McLachlan AD (1961) Mol. Physics 3: 233Google Scholar
  93. 56.
    McConnell HM (1956) J. Chem. Phys. 24: 632Google Scholar
  94. 57.
    McConnell HM, Chesnut DB (1958) ibid. 28: 107Google Scholar
  95. 58.
    Dewar MJS, De Llano C (1969) J. Am. Chem. Soc. 91: 789Google Scholar
  96. 59.
    Tuttle TR, Weissman SI (1958) ibid. 80: 5342Google Scholar
  97. 60.
    Fürderer P, Gerson F, Rabinovitz M, Willner I (1978) Helv. Chim. Acta 61: 2981Google Scholar
  98. 61.
    Fürderer P, Gerson F, Hafner K (1978) ibid. 61: 2974Google Scholar
  99. 62.
    Setzer WN, Schleyer PvR (1985) Advances in Organometallic Chemistry, Vol. 24, 373Google Scholar
  100. 63.
    Brooks JJ, Rhine WE, Stucky GD (1972) J. Am. Chem. Soc. 94: 7396Google Scholar
  101. 64.
    Rhine WE, Davis J, Stucky GD (1975) ibid. 97, 2079Google Scholar
  102. 65.
    Heinze J (1984) Angew. Chem. Int. Ed. Engl. 23: 831Google Scholar
  103. 66.
    Holy NL (1974) Chem. Rev. 74: 243Google Scholar
  104. 67.
    Heilbronner E, Bock H 1976 The HMO Model and Its Applications, Wiley, New YorkGoogle Scholar
  105. 68.
    Hoijtink GJ (1970) Adv. Electrochem. Eng. 7: 221Google Scholar
  106. 69. (a)
    Dietrich M, Mortensen J, Heinze J (1985) Angew. Chem. Int. Ed. Engl. 24: 508Google Scholar
  107. 69. (b)
    Hebert Mazaleyrat JP, Welvart Z (1985) Nouv. J. Chim. 9: 75Google Scholar
  108. 70. (a)
    Stevenson GR, Zigler SS, Reiter RC (1981) J. Am. Chem. Soc. 103: 6057Google Scholar
  109. 70. (b)
    Stevenson GR, Schock LE, Reiter RC (1983) J. Phys. Chem. 87: 4004Google Scholar
  110. 70. (c)
    Stevenson GR, Hashim RT (1986) ibid. 90: 2896 and references cited thereinGoogle Scholar
  111. 71.
    Cope AC, Hochstein FA (1950) J. Am. Chem. Soc. 72: 2515Google Scholar
  112. 72.
    Winstein S, Clippinger E, Fainberg AH, Robinson GC (1954) ibid. 76: 2597Google Scholar
  113. 73.
    Sadek H, Fouss RM (1954) ibid. 76: 5905Google Scholar
  114. 74.
    Smid J (1972) Angew. Chem. Int. Ed. Engl. 11: 112Google Scholar
  115. 75.
    Murdoch JR, Streitwieser A, Jr (1973) Intrascience Chem. Rep. 7: 43Google Scholar
  116. 76.
    Hogen-Esch TE (1977) Advances in Physical Organic Chemistry, Gold V, Bethel D (Eds), Vol. 15, p. 153, Academic Press, LondonGoogle Scholar
  117. 77.
    Stevenson GR, Schock LE, Reiter RC (1984) J. Phys. Chem. 88: 5417Google Scholar
  118. 78. (a)
    Fry AJ, Chung LL, Boekelheide V (1974) Tetrahedron Lett. 445Google Scholar
  119. 78. (b)
    Cox RH, Harrison LW, Austin WK (1973) J. Phys. Chem. 77: 200Google Scholar
  120. 78. (c)
    Strauss HL, Katz TJ, Fraenkel GK (1963) J. Am. Chem. Soc. 85: 2360Google Scholar
  121. 79. (a)
    Smentowski FJ, Stevenson FR (1967) ibid. 89: 5120Google Scholar
  122. 79. (b)
    Smentowski FJ, Stevenson GR (1969) J. Phys. Chem. 73: 340Google Scholar
  123. 79. (c)
    Allendoerfer RD, Rieger PH (1965) J. Am. Chem. Soc. 87: 2336Google Scholar
  124. 79. (d)
    Hogen-Esch TE, Smid J (1965) ibid. 87: 669Google Scholar
  125. 79. (e)
    Hogen-Esch TE, Smid J (1966) ibid. 38: 307Google Scholar
  126. 79. (f)
    Chan LL, Smid J (1967) ibid. 89: 4547Google Scholar
  127. 80.
    Edlund U (1977) Org. Mag. Res. 9: 593Google Scholar
  128. 81.
    Edlund U (1979) ibid. 12: 661Google Scholar
  129. 82. (a)
    Eliasson B, Edlund U (1983) ibid. 21: 322Google Scholar
  130. 82. (b)
    Ahlbrecht H, Schneider G (1986) Tetrahedron 42: 4741Google Scholar
  131. 82. (c)
    Willner I, Becker JY, Rabinovitz M (1979) J. Am. Chem. Soc. 101: 395Google Scholar
  132. 83. (a)
    Eliasson B, Edlund U (1983) J.C.S. Perkin II, 1837Google Scholar
  133. 83. (b)
    Becker BCh, Huber W, Schneiders C, Müllen K (1983) Chem. Ber. 116: 1573Google Scholar
  134. 83. (c)
    Eliasson B, Johnels D, Wold S, Edlund U (1982) Acta Chem. Scand. B 36: 155Google Scholar
  135. 83. (d)
    Edlund U, Sygula A, unpublished resultsGoogle Scholar
  136. 84. (a)
    Streitwieser A, Jr, Swanson JT (1983) J. Am. Chem. Soc. 105: 2502Google Scholar
  137. 84. (b)
    Minsky A, Meyer AY, Hafner K, Rabinovitz M (1983) ibid. 105: 3975Google Scholar
  138. 85. (a)
    Minsky A, Rabinovitz M (1981) Tetrahedron Lett. 22, 5341Google Scholar
  139. 85. (b)
    Mandler D (1986) M.Sc. Thesis, The Hebrew University of JerusalemGoogle Scholar
  140. 86. (a)
    Aromaticity, Chemical Society Special Publications No. 21, London (1967)Google Scholar
  141. 86. (b)
    Breslow R (1965) Chem. Eng. News 43: 90Google Scholar
  142. 86. (c)
    Garratt PJ 1971 Aromaticity, McGraw-Hill, LondonGoogle Scholar
  143. 86. (d)
    Snyder JP (Ed) Non-Benzenoid Aromatics, Vol. I, II, Academic Press, New York, 1969, 1971Google Scholar
  144. 86. (e)
    Lloyd DMG (1966) Carbocyclic Non-Benzenoid Aromatic Compounds, Elsevier Pub. Co. AmsterdamGoogle Scholar
  145. 86. (f)
    Rabinovitz M (Ed) (1980) Isr. J. Chem. 20 Google Scholar
  146. 86. (g)
    Herndon WC (1974) J. Chem. Educ. 51: 10Google Scholar
  147. 87.
    Platt JR (1954) J. Chem. Phys. 22: 1448Google Scholar
  148. 88.
    Randic M (1977) J. Am. Chem. Soc. 99: 444Google Scholar
  149. 89. (a)
    Cresp TM, Sondheimer F (1975) ibid. 97: 4412Google Scholar
  150. 89. (b)
    Rabinovitz M, Willner I (1980) Pure Appl. Chem. 52: 1575Google Scholar
  151. 89. (c)
    Cresp TM, Sondheimer F (1977) J. Am. Chem. Soc. 99: 194Google Scholar
  152. 89. (d)
    Agranat I, Hess BA, Schaad LJ (1980) Pure Appl. Chem. 52: 1399Google Scholar
  153. 90. (a)
    Müllen K, Oth JFM, Engels HW, Vogel E (1979) Angew. Chem. Int. Ed. Engl. 18: 229; (1979) 91: 251Google Scholar
  154. 90. (b)
    Huber W (1983) Tetrahedron Lett. 24: 3595Google Scholar
  155. 91.
    Katz TJ, Rosenberger M, O'Hara RK (1964) J. Am. Chem. Soc. 86: 249; see ref. 61.Google Scholar
  156. 92.
    Edlund U, Eliasson B (1982) J.C.S. Chem. Commun. 950Google Scholar
  157. 93.
    Cox RH, Terry HW, Harrison LW (1971) Tetrahedron Lett. 50: 4815Google Scholar
  158. 94.
    Vogel E, Königshofen H, Wassen J, Müllen K, Oth JFM (1974) Angew. Chem. Int. Ed. Engl. 13: 732; (1974) 86: 777Google Scholar
  159. 95.
    Müllen K (1974) Helv. Chim. acta 57: 2399Google Scholar
  160. 96.
    Vogel E, Engels Hw, Huber W, Lex J, Müllen K (1982) J. Am. Chem. Soc. 104: 3729Google Scholar
  161. 97.
    Huber W, Müllen K, Schneiders C, Iyoda M, Nakagawa M (1986) Helv. Chim. Acta 69: 949Google Scholar
  162. 98.
    Akiyama S, Iyoda M, Nakagawa M (1976) J. Am. Chem. Soc. 98: 6410Google Scholar
  163. 99.
    Nakagawa M (1975) Pure Appl. Chem. 44: 885Google Scholar
  164. 100.
    Lendvai T, Friedl T, Butenschön H, Clark T, de Meijere A (1986) Angew. Chem. Int. Ed. Engl. 25: 718Google Scholar
  165. 101.
    Hafner K (1971) Pure Appl. Chem. 28: 153Google Scholar
  166. 102.
    Dewar MJS 1969 The MO Theory of Organic Chemistry, McGraw-Hill, New York, pp. 152–190Google Scholar
  167. 103. (a)
    Elvidge JA, Jackman LM (1961) J. Chem. Soc. 856Google Scholar
  168. 103. (b)
    Coulson CA, Mallion RB (1976) J. Am. Chem. soc. 98: 592Google Scholar
  169. 104.
    Longuet-Higgins HC 1967 Special Publication No. 21, The Chemical Society; pp. 109–111Google Scholar
  170. 105.
    Aihara J (1979) J. Am. Chem. Soc. 101: 5913Google Scholar
  171. 106.
    Aihara J (1979) ibid. 101: 558Google Scholar
  172. 107.
    Hine J (1966) J. Org. Chem. 31: 1236Google Scholar
  173. 108. (a)
    Neumann G, Müllen K (1986) J. Am. Chem. Soc. 108: 4105Google Scholar
  174. 108. (b)
    Becker BC, Neumann G, Schmickler H, Müllen K (1983) Angew. Chem. Int. Ed. Engl. 22: 241Google Scholar
  175. 109. (a)
    Hafner K (1964) ibid. 3: 165Google Scholar
  176. 109. (b)
    Hafner K (1963) Angew. Chem. 75: 1041Google Scholar
  177. 109. (c)
    Edlund U, Eliasson B, Kowalewski J, Trogen L (1981) J.C.S., Perkin II, 1260Google Scholar
  178. 110.
    Katz TJ, Balogh V, Schulman J (1968) J. Am. Chem. Soc. 90: 734Google Scholar
  179. 111.
    Stowasser B, Hafner K (1986) Angew. Chem. 98: 477Google Scholar
  180. 112.
    Bockelheide V, Vick GK (1956) J. Am. Chem. Soc. 78: 653Google Scholar
  181. 113.
    Huber W (1984) Helv. Chim. Acta 67: 2582Google Scholar
  182. 114.
    Becker BCh, Huber W, Müllen K (1980) J. Am. Chem. Soc. 102: 7803Google Scholar
  183. 115.
    Garratt PJ, Zahler R (1978) ibid. 100: 7753Google Scholar
  184. 116.
    Boche G, Etzrodt H, Marsch M, Thiele W (1982) Angew. Chem. 94: 141Google Scholar
  185. 117.
    Benken R, Finneiser K, v Puttkamer H, Günther H, Elliasson B, Edlund U (1986) Helv. Chim. Acta 69: 955Google Scholar
  186. 118.
    Cremer D, Günther H (1972) Liebigs Ann. 763: 87Google Scholar
  187. 119.
    Berris Bc, Hovakeemian GH, Lai YH, Mestdagh H, Vollhardt KPC (1985) J. Am. Chem. Soc. 107: 5670Google Scholar
  188. 120.
    Rhine WE, Davis JH, Stucky GJ (1977) J. Organometal. Chem. 134: 139Google Scholar
  189. 121.
    Neumann G, Müllen K (1986) Chimia 39; 275Google Scholar
  190. 122.
    Cohen Y, Roelofs NH, Reinhardt G, Scott LT, Rabinovitz M (1987) J. Org. Chem. 52: 4207Google Scholar
  191. 123.
    Scott LT, Reinhardt G, Roelofs NH (1985) J. Org. Chem. 50: 5886Google Scholar
  192. 124.
    Trost BM, Kinson PL (1970) J. Am. Chem. Soc. 92: 2591Google Scholar
  193. 125.
    Trost BM, Kinson PL (1975) ibid. 97: 2438Google Scholar
  194. 126.
    Dagan A, Rabinovitz M (1976) ibid. 98: 8268Google Scholar
  195. 127.
    Katz TJ, Yoshida M, Siew LC (1965) ibid. 87: 4516Google Scholar
  196. 128. (a)
    Günther H, Günther ME, Mondeshka D, Schmikler H (1978) Liebigs Ann. Chem. 165Google Scholar
  197. 128. (b)
    Günther H, Shyoukh A, Cremer D, Frisch KH (1978) 150Google Scholar
  198. 129.
    Müllen K (1978) Helv. Chim. Acta 61: 1296Google Scholar
  199. 130.
    Huber W, May A, Müllen K (1981) Chem. Ber. 114: 1318Google Scholar
  200. 131. (a)
    Huber W, Müllen K (1986) Acc. Chem. Res. 19: 300Google Scholar
  201. 131. (b)
    Heinz W, Langensee P, Müllen K (1987) J.C.S. Chem. Commun. 947Google Scholar
  202. 132.
    Paquette LA, Ewing GD, Traynor S, Gardlick JM (1977) J. Am. Chem. Soc. 99: 6115Google Scholar
  203. 133.
    Staley SW (1981) in: Jones M, Moss RA (Eds) Reactive Intermediates, J. Wiley, New York, Vol. II, pp. 32–34Google Scholar
  204. 134.
    Willner I, Rabinovitz M (1977) J. Am. Chem. Soc. 99: 4507Google Scholar
  205. 135.
    Rabinovitz M, Gazit A (1978) J. Chem. Res. (S) 438; (1978) J. Chem. Res. (M) 5152Google Scholar
  206. 136. (a)
    Staley SW (1981) in: Jones M, Moss RA (Eds) Reactive Intermediates, J. Wiley, New York, Vol. II, pp. 29–30Google Scholar
  207. 136. (b)
    Elliasson B, Edlund U, Rabinovitz M, to be publishedGoogle Scholar
  208. 137. (a)
    Hückel E (1931) Z. Phys. 70: 204Google Scholar
  209. 137. (b)
    Hückel E (1931) ibid. 72: 310Google Scholar
  210. 137. (c)
    Badger GM 1969 Aromatic Character and Aromaticity, CambridgePress, CambridgeGoogle Scholar
  211. 138.
    Clar E 1972 The Aromatic Sextet, Siely-Interscience, New YorkGoogle Scholar
  212. 139.
    Salem L 1969 The Molecular Orbital theory of Organic Chemistry, McGraw-Hill, New YorkGoogle Scholar
  213. 140.
    Ebert LB (1985) in: Ebert LB (Ed) Chemistry of Engine Combustion Deposits, Plenum Publishing Corp., New YorkGoogle Scholar
  214. 141.
    Parker VD (1976) J. Am. Chem. Soc. 98: 98Google Scholar
  215. 142. (a)
    Breslow R (1982) Pure Appl. Chem. 54: 927Google Scholar
  216. 142. (b)
    See ref. 54b, pp. 232–246Google Scholar
  217. 143. (a)
    Willigen HV, Broekhoven JAM, Boer E (1967) Mol. Phys. 12: 533Google Scholar
  218. 143. (b)
    Sommerdijk JL, Boer E (1969) J. Chem. Phys. 50: 4771Google Scholar
  219. 143. (c)
    Jesse RE, Bilven P, Prins R, Vroost JDW, Hoijtink G (1963) J. Mol. Phys. 6: 633Google Scholar
  220. 143. (d)
    Broekhoven JAM, Sommerdijk JL, Boer E (1971) ibid. 20: 993Google Scholar
  221. 143. (e)
    Glasbeek M, Vroost JDW, Hoijtink GJ (1966) J. Chem. Phys. 45: 1852Google Scholar
  222. 143. (f)
    Glasbeek M, Visser AJW, Maas GA, Vroost JDW, Hoijtink GJ (1958) J. Chem. Phys. Lett. 2: 312Google Scholar
  223. 144.
    Bauld NL, Welsher TL, Cessac J, Holloway RL (1978) J. Am. Chem. Soc. 100; 6920Google Scholar
  224. 145.
    Mitchell RD, Bauld NL (1980) Isr. J. Chem. 20: 319Google Scholar
  225. 146. (a)
    Hess BA, Schaad LJ (1971) J. Am. Chem. Soc. 93: 305Google Scholar
  226. 146. (b)
    Hess BA, Schaad LJ (1971) ibid. 93: 2413Google Scholar
  227. 146. (c)
    Randić M (1976) Chem. Phys. Lett. 38: 68Google Scholar
  228. 146. (d)
    Gutman I, Milun M, Trinajstić N (1977) J. Am. Chem. Soc. 99: 1692Google Scholar
  229. 146. (e)
    Illić P, Sinkovć B, Trinajstić N (1980) Isr. J. Chem. 20: 258Google Scholar
  230. 147.
    Haddon RC (1979) J. Am. Chem. Soc. 101: 1722Google Scholar
  231. 148.
    Pople JA, Untch KG (1966) ibid. 88: 4811Google Scholar
  232. 149.
    Van Vleck JH 1932 Electric and Magnetic Susceptibilities, Oxford University Press, pp. 262–276Google Scholar
  233. 150.
    Paul DE, Lipkin D, Weissman SI (1956) J. Am. Chem. Soc. 78: 116Google Scholar
  234. 151.
    Sternberg HW, Delle Donne CL, Pantages P, Moroni EC, Markby RE (1971) Fuel 50: 432Google Scholar
  235. 152.
    Tuttle TR, Ward RL, Wiessman SI (1956) J. Chem. Phys. 25: 189Google Scholar
  236. 153.
    Hendricks BMP, Canters GW, Corvaja C, de Beor JWM, de Boer E (1971) Mol. Phys. 20: 193Google Scholar
  237. 154.
    Henrici-Olive G, Olive S (1964) Zeit, Phys. Chem. 43: 340Google Scholar
  238. 155.
    Smid J (1965) J. Am. Chem. Soc. 87: 655Google Scholar
  239. 156.
    Carnahan Jc, Closson WD (1972) J. Org. Chem. 34: 4469Google Scholar
  240. 157.
    Gia HB, Jerome R, Teyssie Ph (1980) J. Organomet. Chem. 190: 107Google Scholar
  241. 158.
    Bank S, Bockrath B (1971) J. Am. Chem. Soc. 93: 430Google Scholar
  242. 159.
    Minsky A, Rabinovitz M (1983) Synthesis 6: 497Google Scholar
  243. 160.
    Minsky A, Rabinovitz M (1984) J. Am. Chem. Soc. 106: 6755Google Scholar
  244. 161.
    Fraenkel Y 1986 M.Sc. Thesis, The Hebrew University of JerusalemGoogle Scholar
  245. 162.
    Glidewell C, Lloyd D (1986) Chimica Scripta 26: 373Google Scholar
  246. 163.
    Glidewell C, Lloyd D (1984) Tetrahedron 40: 4455Google Scholar
  247. 164.
    Glidewell C, Lloyd D (1987) J. Chem. Ed. (in press)Google Scholar
  248. 165.
    Ebert LB see reference 140; pp. 303Google Scholar
  249. 166.
    Randić M (1982) J. Phys. Chem. 86: 3970Google Scholar
  250. 167. (a)
    Levine G, Sutphen C, Szwarc M (1972) J. Am. Chem. Soc. 94: 2653Google Scholar
  251. 167. (b)
    Rabideau PW, Borkholder EG (1978) J. Org. Chem. 43: 4283Google Scholar
  252. 167. (c)
    Sargent Gd, Cron JN, Bank S (1966) J. Am. Chem. Soc. 88: 5363Google Scholar
  253. 167. (d)
    Sargent GD, Lux GA (1968) ibid. 90: 7160Google Scholar
  254. 167. (e)
    Grast JF, Roberts Rd, Abeles BN (1975) ibid. 97: 4925Google Scholar
  255. 167. (f)
    Guysten H, Horner L (1962) Angew. Chem. Int. Ed., Engl. 1: 455Google Scholar
  256. 168. (a)
    Harvey RG (1970) Synthesis 2: 161Google Scholar
  257. 168. (b)
    Harvey RG, Arzadon L (1969) Tetrahedron 25: 4887Google Scholar
  258. 169. (a)
    Rabideau PW, Harvey RG (1970) J. Org. Chem. 35: 25Google Scholar
  259. 169. (b)
    Rabideau PW, Wetzel DM, Husted CA, Lawrence JR (1984) Tetrahedron Lett. 25: 31Google Scholar
  260. 170. (a)
    Müllen K, Huber W, Neumann G, Schneiders C, Unterberg H (1985) J. Am. Chem. Soc. 107: 801Google Scholar
  261. 170. (b)
    Müllen K (1987) Angew. Chem. Int. Ed. Engl. 26: 204Google Scholar
  262. 171. (a)
    Minsky A, Meyer AY, Rabinovitz M (1982) J. Am. Chem. Soc. 104: 2475Google Scholar
  263. 171. (b)
    Minsky A, Klein J, Rabinovitz M (1981) ibid. 103: 4586Google Scholar
  264. 172.
    Eliasson B, Lejon T, Edlund U (1984) J.C.S. Chem. Commun. 591Google Scholar
  265. 173.
    Ebert LB (1986) Tetrahedron 42: 497Google Scholar
  266. 174.
    Lebedev YS, Sidorov AN (1981) Russ. J. Phys. Chem. (Engl. Transl.) 55: 1220Google Scholar
  267. 175.
    Smith JG, Levi EM (1972) J. Organomet. Chem. 36: 215Google Scholar
  268. 176.
    Kaban S, Smith JG (1983) Organometallics 2: 1251Google Scholar
  269. 177. (a)
    Paquette LA, Hansen Jf, Kakihana R (1971) J. Am. Chem. Soc. 93: 168Google Scholar
  270. 177. (b)
    Stevenson GR, Shock LE, Reiter Rc, Hanson JF (1983) ibid. 105: 6078Google Scholar
  271. 177. (c)
    Buncel E 1980 in: Comprehensive Carbanion Chemistry, Elsevier, Amsterdam part A, p. 35Google Scholar
  272. 177. (d)
    Van Broekhoven JAM, Sommerdijk JT, De Beor E (1971) Mol. Phys. 20: 993Google Scholar
  273. 178.
    Minsky A, Cohen Y, Rabinovitz M (1985) J. Am. Chem. Soc. 107: 1501Google Scholar
  274. 179.
    Cohen Y, Meyer AY, Rabinovitz M (1986) ibid. 108: 7039Google Scholar
  275. 180. (a)
    Rabinovitz M, Cohen Y (1987) Ebert L (Ed) in: ACS Advances in Chemistry Series No. 217, Chemistry of Polynuclear AromaticsGoogle Scholar
  276. 180. (b)
    Eisch JJ (1986) in: Preprints Div. of Fuel Chem., ACS 31 (4): 798Google Scholar
  277. 180. (c)
    Rabinovitz M, Cohen Y (1986) in: Preprints Div. of Fuel Chem., ACS 31(4): 777Google Scholar
  278. 181.
    Tamarkin D, Cohen Y, Rabinovitz M (1987) Synthesis 196Google Scholar
  279. 182.
    Ebert LB, Mills DR, Scanlon JC, Symposium on Advances in Resid Upgrading, ACS Meeting Denver, Colorado, April 5–10, 1987, pp. 419Google Scholar
  280. 183.
    Sternberg HW, Delle Donne CL, Markby Re, Friedman S (1974) Ind. Eng. Chem./Process Res. Div. 13: 433Google Scholar
  281. 184.
    Cohen Y, Klein J, Rabinovitz M (1985) J.C.S., Chem. Commun. 1033Google Scholar
  282. 185.
    Cohen Y, Klein J, Rabinovitz M (1987) J.C.S. Perkin 2 (in the press)Google Scholar
  283. 186.
    Cohen Y, Klein J, Rabinovitz M, J.C.S. Chem. Commun., in the pressGoogle Scholar
  284. 187.
    Palmer MH, Kennedy SMF (1976) J.C.S. Perkin 2: 81Google Scholar
  285. 188.
    Stille WC, Sreekumar C (1980) J. Am. Chem. Soc. 102: 1201Google Scholar
  286. 189.
    Smith Jg, McCall RB (1980) J. Org. Chem. 45: 3982Google Scholar
  287. 190.
    Müllen K, Unterberg H, Huber W, Wennerstrom O, Norinder U, Tanner D, Thulin B (1984) J. Am. Chem. Soc. 106: 7514Google Scholar
  288. 191.
    Frim R, Raulfs FW, Hopf H, Rabinovitz M (1986) Angew. Chem., Int. Edit. Engl. 25: 174Google Scholar
  289. 192. (a)
    Boekelhelde V (1980) Acc. Chem. Res. 13: 65Google Scholar
  290. 192. (b)
    Hopf H, Klein-Schroth J (1982) Angew. Chem. 94: 485; (1982) Angew. Chem. Int. Ed. 21: 469Google Scholar
  291. 192. (c)
    Boekelheide V (1983) Top. Curr. Chem. 113: 87Google Scholar
  292. 192. (d)
    Hopf H (1983) in: Keehn PM, Rosenfeld SM (Eds), Cyclophanes, Academic Press, N.Y., p. 21Google Scholar
  293. 192. (e)
    Heilbronner E, Yang ZZ (1984) Top. Curr. Chem. 115: 1Google Scholar
  294. 192. (f)
    Gerson F (1984) ibid. 225: 57Google Scholar
  295. 192. (g)
    Swann Rt, Hanson AW, Boekelheide V (1986) J. Am. Chem. Soc. 108: 3324Google Scholar
  296. 193. (a)
    Hopf H, Mlynek C, El Tamany S, Ernst L (1985) ibid. 107: 6620Google Scholar
  297. 193. (b)
    Swann RT, Hanson AW, Boekelheide V (1986) ibid. 108: 3324Google Scholar
  298. 193. (c)
    Hopf H (1983) Naturwissenschaften 70: 349Google Scholar
  299. 194.
    Haenel MW (1977) Tetrahedron Lett. 1273Google Scholar
  300. 195.
    Private communication from Professor K. Hafner — Bickert, P.: dissertation, Technische Hochschule Darmstadt 1983Google Scholar
  301. 196.
    Hopf H, Raulfs F-W, Schonburg D (1986) Tetrahedron 42: 1655Google Scholar
  302. 197.
    Frim R, Rabinovitz M, Hopf H, Hucker J (1987) Angew. Chem. Int. Ed. Engl. 26: 232Google Scholar
  303. 198.
    Clar E, Zander M (1957) J. Chem. Soc. 4616Google Scholar
  304. 199.
    Diedrich F, Staab HA (1978) Angew. Chem. 90: 383Google Scholar
  305. 200. (a)
    Thulin B, Wennerström O (1976) Acta Chem. Scand. B 30: 369Google Scholar
  306. 200. (b)
    Anker K, Lamm B, Thulin B, Wennerström O (1978) ibid. 32: 155Google Scholar
  307. 201. (a)
    Huber W, Müllen K, Wennerström O (1980) Angew. Chem. 92: 636Google Scholar
  308. 202.
    Tanner D, Wennerström O, Nordiner U, Müllen K, Trinks R (1986) Tetrahedron 42: 4499Google Scholar
  309. 203.
    Nordiner U, Wennerström O, Wennerström H (1984) Tetrahedron Lett. 1397Google Scholar
  310. 204.
    Bieber W, Vögtle F (1977) Angew. Chem. 89: 199Google Scholar
  311. 205. (a)
    Gerson F, Heckendorn R, Möckel R, Vögtle F (1985) H.C.A. 68: 1923Google Scholar
  312. 205. (b)
    Gerson F, Huber W (1987) Acc. Chem. Res. 20: 85Google Scholar

Copyright information

© Springer-Verlag 1988

Authors and Affiliations

  • Mordecai Rabinovitz
    • 1
  1. 1.Department of Organic ChemistryThe Hebrew University of JerusalemJerusalemIsrael

Personalised recommendations