Advertisement

Angle strained cycloalkynes

Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 109)

Keywords

Bond Angle High Occupied Molecular Orbital Triple Bond Lower Unoccupied Molecular Orbital Energy High Occupied Molecular Orbital Energy 
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)
    The literature is covered until June 1982, in few cases later references are included. Previous reviews on this topic or parts of it are: R. W. Hoffmann: Dehydrobenzene and Cycloalkynes, Verlag Chemie, Weinheim 1967Google Scholar
  2. 1. b)
    A. Krebs: Cyclic Acetylenes, in: Chemistry of Acetylenes, (Ed. H. G. Viehe), Marcel Dekker, New York 1969, p. 987Google Scholar
  3. 1. c)
    M. Nakagawa: Cyclic Acetylenes, in: The Chemistry of the carbon-carbon triple bond, (Ed. S. Patai), J. Wiley & Sons, New Aork 1978, p. 635Google Scholar
  4. 1. d)
    H. Meier, Synthesis 1972, 235.Google Scholar
  5. 3.
    P. Saxe, H. F. Schaefer III: J. Am. Chem. Soc. 102, 3239 (1980)CrossRefGoogle Scholar
  6. 4.
    W. R. Moore, H. R. Ward: ibid. 85, 86 (1963)CrossRefGoogle Scholar
  7. 5.
    W. J. Ball, S. R. Landor: Proc. Chem. Soc. 1961, 143Google Scholar
  8. 6.
    A. T. Blomquist, L. H. Liu, J. C. Bohrer: J. Am. Chem. Soc. 74, 3643 (1952)CrossRefGoogle Scholar
  9. 7.
    H. Meier, E. Voigt: Tetrahedron 28, 187 (1972)CrossRefGoogle Scholar
  10. 8.
    A. Krebs, H. Kimling: Angew. Chem. 83, 540 (1971); Angew. Chem. Int. Edit. 10, 509 (1971)Google Scholar
  11. 9.
    J. Pocklington: Ph.D. Thesis Hamburg, 1979Google Scholar
  12. 10.
    L. K. Montgomery, L. E. Applegate: J. Am. Chem. Soc. 89, 5305 (1967)CrossRefGoogle Scholar
  13. 11.
    L. Brandsma, H. D. Verkruijsse: Synthesis 1978, 290Google Scholar
  14. 12.
    A. Krebs, W. Cholcha: unpublished resultsGoogle Scholar
  15. 13.
    O. L. Chapman, J. Gano, P. R. West, M. Regitz, G. Maas: J. Am. Chem. Soc. 103, 7033 (1981)CrossRefGoogle Scholar
  16. 14.
    G. Wittig, I. Meske-Schüller: Liebigs Ann. Chem. 711, 65 (1968)Google Scholar
  17. 15.
    A. Krebs: Angew. Chem. 77, 966 (1965); Angew. Chem. Int. Ed. Engl. 4, 953 (1965); A. Krebs, D. Byrd: Lieb. Ann. Chem. 707, 66 (1967)Google Scholar
  18. 16.
    A. S. Lankey, M. A. Ogliaruso: J. Org. Chem. 36, 3339 (1971)CrossRefGoogle Scholar
  19. 17.
    G. Wittig, A. Krebs, R. Pohlke: Angew. Chem. 72, 324 (1960)Google Scholar
  20. 18.
    G. Wittig, A. Krebs: Chem. Ber. 94, 3260 (1961)Google Scholar
  21. 19.
    G. Wittig, R. Pohlke: ibid. 94, 3276 (1961)Google Scholar
  22. 20.
    G. Wittig, J. Weinlich, E. R. Wilson: ibid. 98, 458 (1965)Google Scholar
  23. 21.
    G. Wittig, J. Heyn: Liebigs Ann. Chem. 726, 57 (1969)Google Scholar
  24. 22.
    G. Wittig, J. Heyn: ibid. 756, 1 (1972)Google Scholar
  25. 23.
    L. K. Montgomery, J. D. Roberts: J. Am. Chem. Soc. 82, 4750 (1960)CrossRefGoogle Scholar
  26. 24.
    L. K. Montgomery, F. Scardiglia, J. D. Roberts: ibid. 87, 1917 (1965)CrossRefGoogle Scholar
  27. 25.
    J. M. Bolster, R. M. Kellogg: ibid. 103, 2868 (1981)CrossRefGoogle Scholar
  28. 26.
    G. Wittig, H. Heyn: Chem. Ber. 97, 1609 (1964)Google Scholar
  29. 27.
    K. L. Erickson, J. Wolinsky: J. Am. Chem. Soc. 87, 1142 (1965)CrossRefGoogle Scholar
  30. 28.
    K. L. Erickson, B. E. Vanderwaart, J. Wolinsky: J.C.S. Chem. Commun. 1968, 1031Google Scholar
  31. 29.
    L. Fitjer, U. Kliebisch, D. Wehle, S. Modaressi: Tetrahedron Lett. 1982, 1661Google Scholar
  32. 30.
    P. G. Gassman, T. J. Atkins: ibid. 1975, 3035Google Scholar
  33. 31.
    P. G. Gassman, J. J. Valcho: J. Am. Chem. Soc. 97, 4768 (1975)CrossRefGoogle Scholar
  34. 32.
    P. G. Gassman, I. Gennick: ibid. 102, 6863 (1980)CrossRefGoogle Scholar
  35. 33.
    J. Nakayama, T. Segiri, R. Ohya, M. Hoshino: J.C.S. Chem. Comm. 1980, 791Google Scholar
  36. 34.
    F. Scardiglia, J. D. Roberts: Tetrahedron 1, 343 (1957)CrossRefGoogle Scholar
  37. 35.
    A. T. Bottini, F. P. Corson, R. Fitzgerald, K. A. Frost II: ibid. 28, 4883 (1972)CrossRefGoogle Scholar
  38. 36.
    P. Caubère, J. J. Brunet: ibid. 29, 4835 (1972)CrossRefGoogle Scholar
  39. 37.
    B. Fixari, J. J. Brunet, P. Caubère: ibid. 32, 927 (1976)CrossRefGoogle Scholar
  40. 38.
    D. E. Applequist, P. A. Gebauer, D. E. Gwynn, L. H. O'Connor: J. Am. Chem. Soc. 94, 4272 (1972)CrossRefGoogle Scholar
  41. 39.
    C. N. Bush, D. E. Applequist: J. Org. Chem. 42, 1076 (1977)CrossRefGoogle Scholar
  42. 40.
    G. Wittig, U. Mayer: Chem. Ber. 96, 329 (1963)Google Scholar
  43. 41.
    G. Wittig, U. Mayer: ibid. 96, 342 (1963)Google Scholar
  44. 42.
    G. Wittig, J. Weinlich: ibid. 98, 471 (1965)Google Scholar
  45. 43.
    J. Wolinsky: J. Org. Chem. 26, 704 (1961)CrossRefGoogle Scholar
  46. 44.
    J. J. Brunet, B. Fixari, P. Caubère: Tetrahedron 30, 2931 (1974)CrossRefGoogle Scholar
  47. 45.
    A. T. Bottini, B. R. Anderson, V. Dev, K. A. Frost jr.: ibid. 32, 1613 (1976)CrossRefGoogle Scholar
  48. 46.
    M. A. Bennett, G. B. Robertson, P. O. Whimp, T. Yoshida: J. Am. Chem. Soc. 93, 3797 (1971)CrossRefGoogle Scholar
  49. 47.
    M. A. Bennett, T. Yoshida: ibid. 100, 1750 (1978)CrossRefGoogle Scholar
  50. 48.
    C. F. Huebner, R. T. Puckett, M. Brzechffa, S. L. Schwartz: Tetrahedron Lett. 1970, 359Google Scholar
  51. 49.
    H. Hart, S. Shamouilian, Y. Takehira: J. Org. Chem. 46, 4427 (1981)CrossRefGoogle Scholar
  52. 50.
    J. G. Duboudin, B. Jousseaume, M. Pinet-Vallier: J. Organomet. Chem. 172, 1 (1979)CrossRefGoogle Scholar
  53. 51.
    E. Müller, G. Odenigbo: Chemiker-Ztg. 97, 662 (1973)Google Scholar
  54. 52.
    E. Müller, G. Odenigbo: Liebigs Ann. Chem. 1975, 1435Google Scholar
  55. 53.
    A. Faworsky, W. Boshowsky: ibid. 390, 122 (1912)Google Scholar
  56. 54.
    A. Favorsky, N. A. Domnine, M. F. Chestakowski: Bull. Soc. Chim. France [5] 3, 1727 (1936)Google Scholar
  57. 55.
    A. T. Bottini, K. A. Frost II, B. R. Anderson, V. Dev.: Tetrahedron 29, 1975 (1973)CrossRefGoogle Scholar
  58. 56.
    R. Breslow, J. Posner, A. Krebs: J. Am. Chem. Soc. 85, 234 (1963)CrossRefGoogle Scholar
  59. 57.
    R. Breslow, L. J. Altman, A. Krebs, E. Mohacsi, I. Murata, R. A. Peterson, J. Posner: ibid. 87, 1326 (1965)CrossRefGoogle Scholar
  60. 58.
    H. Meier, M. Layer, W. Combrink, S. Schniepp: Chem. Ber. 109, 1650 (1976)Google Scholar
  61. 59.
    F. G. Willey: Angew. Chem. 76, 144 (1964); Angew. Chem. Int. Ed. 3, 138 (1964)Google Scholar
  62. 60.
    A. Güntner: Diplom Thesis, Hamburg 1982Google Scholar
  63. 61.
    H. Meier, T. Molz, U. Merkle, T. Echter, M. Lorch: Liebigs Ann. Chem. 1982, 914Google Scholar
  64. 62.
    A. Krebs, G. Burgdörfer: Tetrahedron Lett. 1973, 2063Google Scholar
  65. 63.
    G. Burgdörfer: Ph. D. Thesis, Heidelberg 1975Google Scholar
  66. 64.
    S. F. Karaev, A. Krebs: Tetrahedron Lett. 1973, 2853Google Scholar
  67. 65.
    H. J. Hohlt: Ph. D. Thesis, Hamburg 1981Google Scholar
  68. 66.
    W. Tochtermann: Angew. Chem. 74, 432 (1962)Google Scholar
  69. 67.
    W. Tochtermann, K. Oppenländer, U. Walter: Chem. Ber. 97, 1318, 1329 (1964)Google Scholar
  70. 68.
    W. Tochtermann, K. Oppenländer, M. N. D. Hoang: Liebigs Ann. Chem. 701, 117 (1967)Google Scholar
  71. 69.
    M. Lorch, H. Meier: Chem. Ber. 114, 2382 (1981)Google Scholar
  72. 70.
    J. Odenthal: Ph. D. Thesis, Heidelberg 1975Google Scholar
  73. 71.
    J. A. Elix, M. V. Sargent: J. Am. Chem. Soc. 91, 4734 (1969)Google Scholar
  74. 72.
    J. A. Elix, M. V. Sargent, F. Sondheimer: J.C.S. Chem. Commun. 1966, 509Google Scholar
  75. 73.
    J. F. M. Oth, R. Merenyi, T. Martini, G. Schröder: Tetrahedron Lett. 1966, 3087Google Scholar
  76. 74.
    J. Gasteiger, G. E. Gream, R. Huisgen, W. E. Konz, U. Schnegg: Chem. Ber. 104, 2412 (1971)Google Scholar
  77. 75.
    H. N. C. Wong, F. Sondheimer: Tetrahedron Lett. 1980, 983Google Scholar
  78. 76.
    H. N. C. Wong, F. Sondheimer: J. Org. Chem. 45, 2438 (1980)CrossRefGoogle Scholar
  79. 77.
    H. Gugel, H. Meier: Chem. Ber. 113, 1431 (1980)Google Scholar
  80. 78.
    H. N. C. Wong: Ph. D. Thesis, Univ. College London, 1976 cited in 79)Google Scholar
  81. 79.
    N. Z. Huang, F. Sondheimer: Acc. Chem. Res. 15, 96 (1982)Google Scholar
  82. 80.
    P. E. Eaton, C. E. Stubbs: J. Am. Chem. Soc. 89, 3722 (1967)Google Scholar
  83. 81.
    R. Wolovsky, F. Sondheimer: ibid. 88, 1525 (1966)CrossRefGoogle Scholar
  84. 82.
    W. A. Böll: Angew. Chem. 78, 755 (1966); Angew. Chem. Int. Ed. 5, 733 (1966)Google Scholar
  85. 83.
    M. Psiorz, H. Hopf: Angew. Chem. 94, 639 (1982); Angew. Chem. Int. Ed. Engl. 21, 623 (1982)Google Scholar
  86. 84.
    A. Krebs, H. Kimling: Tetrahedron Lett. 1970, 761Google Scholar
  87. 85.
    A. Krebs, H. Kimling: Liebigs Ann. Chem. 1974, 2074Google Scholar
  88. 86.
    U. Höpfner: Ph. D. Thesis, Heidelberg 1979Google Scholar
  89. 87.
    R. Neubauer: Ph. D. Thesis, Heidelberg 1977Google Scholar
  90. 88.
    C. Santiago, K. N. Houk, G. J. De Cicco, L. T. Scott: J. Am. Chem. Soc. 100, 692 (1978)CrossRefGoogle Scholar
  91. 89.
    A. T. Blomquist, L. H. Liu: ibid. 75, 2153 (1953)CrossRefGoogle Scholar
  92. 90.
    G. Schröder, J. F. M. Oth: Angew. Chem. 79, 458 (1967); Angew. Chem. Int. Ed. Engl. 6, 414 (1967)Google Scholar
  93. 91.
    G. Schröder, H. Röttele, R. Merenyi, J. F. M. Oth: Chem. Ber. 100, 3527 (1967)Google Scholar
  94. 92.
    J. F. M. Oth, R. Merenyi, H. Röttele, G. Schröder: ibid. 100, 3538 (1967)Google Scholar
  95. 93.
    G. Wittig, H.-L. Dorsch: Liebigs Ann. Chem. 711, 46 (1968)Google Scholar
  96. 94.
    Eu. Müller, H. Meier: ibid. 716, 11 (1968)Google Scholar
  97. 95.
    H. Meier, I. Menzel: J.C.S. Chem. Commun. 1971, 1059Google Scholar
  98. 96.
    E. V. Dehmlow, M. Lissel: Liebigs Ann. Chem. 1980, 1Google Scholar
  99. 97.
    H. Meier, I. Menzel: Synthesis 1971, 215Google Scholar
  100. 98.
    A. Krebs, K. D. Seidel: unpublished resultsGoogle Scholar
  101. 99.
    A. Krebs: unpublished resultsGoogle Scholar
  102. 100.
    A. Krebs: Tetrahedron Lett. 1968, 4511Google Scholar
  103. 101.
    A. Krebs, U. Joerss: unpublished resultsGoogle Scholar
  104. 102.
    J. Deutsch: Ph. D. Thesis, Heidelberg 1979Google Scholar
  105. 103.
    E. Kloster-Jensen, J. Wirz: Angew. Chem. 85, 723 (1973); Angew. Chem. Int. Ed. Engl. 12, 671 (1973)Google Scholar
  106. 104.
    E. Kloster-Jensen, J. Wirz: Helv. Chim. Acta 58, 162 (1975)CrossRefGoogle Scholar
  107. 105.
    H. Meier, C. Schulz-Popitz, H. Petersen: Angew. Chem. 93, 286 (1981); Angew. Chem. Int. Ed. Engl. 20, 270 (1981)Google Scholar
  108. 106.
    H. Petersen, H. Kolshorn, H. Meier: Angew. Chem. 90, 483 (1978); Angew. Chem. Int. Ed. Engl. 17, 461 (1978)Google Scholar
  109. 107.
    W. Leupin, J. Wirz: Helv. Chim. Acta 61, 1663 (1978)CrossRefGoogle Scholar
  110. 108.
    H. Petersen, H. Meier: Chem. Ber. 113, 2383 (1980)Google Scholar
  111. 109.
    H. Meier, T. Echter, H. Petersen: Angew. Chem. 90, 997 (1978); Angew. Chem. Int. Ed. Engl. 17, 942 (1978)Google Scholar
  112. 110.
    H. Bühl, H. Gugel, H. Kolshorn, H. Meier: Synthesis 1978, 536Google Scholar
  113. 111.
    H. Meier, N. Hanold, H. Kolshorn: Angew. Chem. 94, 67 (1982); Angew. Chem. Int. Ed. Engl. 21, 66 (1982)Google Scholar
  114. 112.
    H. Meier, T. Echter: Angew. Chem. 94, 68 (1982); Angew. Chem. Int. Ed. Engl. 21, 67 (1982)Google Scholar
  115. 113.
    C. B. Reese, A. Shaw: J.C.S. Chem. Commun. 1970, 1172Google Scholar
  116. 114.
    C. B. Reese, A. Shaw: J.C.S. Perkin I 1975, 2422Google Scholar
  117. 115.
    H. Meier, H. Petersen: Chem. Ber. 111, 3423 (1978)Google Scholar
  118. 116.
    H. Hanack, W. Spang: ibid. 113, 2015 (1980)Google Scholar
  119. 117.
    H. Meier, M. Layer, A. Zetzsche: Chemiker-Ztg. 98, 460 (1974)Google Scholar
  120. 118.
    A. Krebs, J. Oldenthal, H. Kimling: Tetrahedron Lett. 1975, 4663Google Scholar
  121. 119.
    H. N. C. Wong, F. Sondheimer: Angew. Chem. 88, 126 (1976); Angew. Chem. Int. Ed. Engl. 15, 117 (1976)Google Scholar
  122. 120.
    G. Seitz, L. Pohl, R. Pohlke: Angew. Chem. 81, 427 (1969); Angew. Chem. Int. Ed. Engl. 8, 447 (1969)Google Scholar
  123. 121.
    H. Meier, H. Gugel: Synthesis 1976, 338Google Scholar
  124. 122.
    H. N. C. Wong, P. J. Garratt, F. Sondheimer: J. Am. Chem. Soc. 96, 5604 (1974)CrossRefGoogle Scholar
  125. 123.
    H. N. C. Wong, F. Sondheimer: Tetrahedron 37, 99 (1981)CrossRefGoogle Scholar
  126. 124.
    C. B. Reese, A. Shaw: J.C.S. Chem. Commun. 1972, 787Google Scholar
  127. 125.
    C. B. Reese, H. P. Sanders: Synthesis 1981, 276Google Scholar
  128. 126.
    V. Prelog, K. Schenker, W. Küng: Helv. Chim. Acta 36, 471 (1953)CrossRefGoogle Scholar
  129. 127.
    A. C. Cope, M. W. Fordice: J. Am. Chem. Soc. 89, 6187 (1967)CrossRefGoogle Scholar
  130. 128.
    R. D. Miller: Ph.D. Thesis, Cornell Univ., Ithaca, N.Y. 1968Google Scholar
  131. 129.
    K. Grohmann, F. Sondheimer: Tetrahedron Lett. 1967, 3121Google Scholar
  132. 130.
    A. J. Hubert, J. Dale: J. Chem. Soc. 1963, 86Google Scholar
  133. 131.
    R. Wolovsky, F. Sondheimer: J. Am. Chem. Soc. 84, 2844 (1962)CrossRefGoogle Scholar
  134. 132.
    R. Wolovsky, F. Sondheimer: ibid. 87, 5720 (1965)CrossRefGoogle Scholar
  135. 133.
    F. Sondheimer, R. Wolovsky, P. J. Garratt, I. C. Calder: ibid. 88, 2610 (1966)CrossRefGoogle Scholar
  136. 134.
    L. T. Scott, G. J. DeCicco: Tetrahedron Lett. 1976, 2663Google Scholar
  137. 135.
    G. Büchi, K. C. T. Luk: J. Org. Chem. 43, 168 (1978)CrossRefGoogle Scholar
  138. 136.
    O. M. Behr, G. Eglington, R. A. Raphael: Chem. and Ind. 1959, 699Google Scholar
  139. 137.
    O. M. Behr, G. Eglington, A. R. Galbraith, R. A. Raphael: J. Chem. Soc. 1960, 3614Google Scholar
  140. 138.
    O. M. Behr, G. Eglington, I. A. Lardy, R. A. Raphael: ibid. 1964, 1151Google Scholar
  141. 139.
    G. M. Pilling, F. Sondheimer: J. Am. Chem. Soc. 93, 1970 (1971)CrossRefGoogle Scholar
  142. 140.
    T. Matsuoka, T. Negi, T. Otsubo, Y. Sakata, S. Misumi: Bull. Chem. Soc. Japan 45, 1825 (1972)Google Scholar
  143. 141.
    T. Matsuoka, T. Negi, S. Misumi: Synthetic Commun. 2, 87 (1972)Google Scholar
  144. 142.
    G. L. Lange, T. W. Hall: J. Org. Chem. 39, 3819 (1974)CrossRefGoogle Scholar
  145. 143.
    Many aspects of angle strain and other kinds of strain are discussed in: A. Greenberg, J. F. Liebman: Strained Organic Molecules, Academic Press, New York 1978Google Scholar
  146. 144.
    H. Meier, H. Petersen, H. Kolshorn: Chem. Ber. 113, 2398 (1980)Google Scholar
  147. 145.
    H. J. Hohlt, A. Krebs, R. Machinek, W. Lüttke, V. Sinnwell: unpublished resultsGoogle Scholar
  148. 146.
    A. Krebs, W. Rüger, L. Ng, K. D. Jordan: Bull. Soc. Chim. Belg. 91, 363 (1982)Google Scholar
  149. 147.
    L. Ng, K. D. Jordan, A. Krebs, W. Rüger: J. Am. Chem. Soc. 104, 7414 (1982)CrossRefGoogle Scholar
  150. 148.
    C. Batich, O. Ermer, E. Heilbronner, J. R. Wiseman: Angew. Chem. 85, 302 (1973); Angew. Chem. Int. Ed. Engl. 12, 312 (1973)Google Scholar
  151. 149.
    H. Schmidt, A. Schweig, A. Krebs: Tetrahedron Lett. 1974, 1471Google Scholar
  152. 150.
    R. B. Turner, A. D. Jarrett, P. Goebel, B. J. Mallon: J. Am. Chem. Soc. 95, 790 (1973)CrossRefGoogle Scholar
  153. 151.
    W. R. Roth, H. W. Lennartz: unpublished resultsGoogle Scholar
  154. 152.
    N. L. Allinger, A. Y. Meyer: Tetrahedron 31, 1807 (1975)CrossRefGoogle Scholar
  155. 153.
    F. A. L. Anet, I. Yavari: ibid. 34, 2879 (1978)CrossRefGoogle Scholar
  156. 154.
    D. W. Garrett: Ph.D. Thesis, Indiana Univ., Bloomington 1974Google Scholar
  157. 155.
    G. Wittig, P. Fritze: Liebigs Ann. Chem. 711, 82 (1968)Google Scholar
  158. 156.
    G. Wittig, J. Meske-Schüller: ibid. 711, 76 (1968)Google Scholar
  159. 157.
    R. A. G. de Graff, S. Gortner, C. Romers, H. N. C. Wong, F. Sondheimer: J. Chem. Soc. Perkin. Trans. II 1981, 478Google Scholar
  160. 158.
    R. Destro, T. Pilati, M. Simonetta: J. Am. Chem. Soc. 97, 658 (1975)CrossRefGoogle Scholar
  161. 159.
    R. Destro, T. Pilati, M. Simonetta: Acta Cryst. Sect. B B 33, 447 (1977)CrossRefGoogle Scholar
  162. 160.
    V. Typke, J. Haase, A. Krebs: J. Mol. Struct. 56, 77 (1979)CrossRefGoogle Scholar
  163. 161.
    J. Haase, A. Krebs: Z. Naturforsch. 26a, 1190 (1971)Google Scholar
  164. 162.
    J. Haase, A. Krebs: ibid. 27a, 624 (1972)Google Scholar
  165. 163.
    H. H. Bartsch, H. Colberg, A. Krebs: Z. Kristallogr. 156, 10 (1981)Google Scholar
  166. 164.
    C. Römming: unpublished results, cited in 104)Google Scholar
  167. 165.
    M. K. Au, T. W. Siu, T. C. W. Mak, T. L. Chan: Tetrahedron Lett. 1978, 4269Google Scholar
  168. 166.
    C. Romers, T. L. Chan: unpublished results, cited in 79)Google Scholar
  169. 167.
    W. K. Grant, J. C. Speakman: Proc. Chem. Soc. 1959, 231Google Scholar
  170. 168.
    R. Weiss: Ph.D. Thesis, Univ. of California, Los Angeles 1976; cited in88) Google Scholar
  171. 169.
    D. W. Rogers, F. J. McLafferty: Tetrahedron 27, 3765 (1971)CrossRefGoogle Scholar
  172. 170.
    R. B. Turner, B. J. Mallon, M. Tichy, W. von E. Doering, W. R. Roth, G. Schröder: J. Am. Chem. Soc. 95, 8605 (1973)CrossRefGoogle Scholar
  173. 171.
    R. B. Turner, D. E. Nettleton, Jr., M. Perelman: ibid. 80, 1430 (1958)CrossRefGoogle Scholar
  174. 172.
    G. Wittig, P. Fritze: Angew. Chem. 78, 905 (1966); Angew. Chem. Int. Ed. Engl. 5, 846 (1966)Google Scholar
  175. 173.
    E. T. Marquis, P. D. Gardner: Tetrahedron Lett. 1966, 2793Google Scholar
  176. 174.
    J. P. Visser, J. E. Ramakers: J.C.S. Chem. Commun. 1972, 178Google Scholar
  177. 175.
    R. Hoffmann, A. Imamura, W. J. Hehre: J. Am. Chem. Soc. 90, 1499 (1968)CrossRefGoogle Scholar
  178. 176.
    E. Haselbach: Helv. Chim. Acta 54, 1981 (1971)CrossRefGoogle Scholar
  179. 177.
    G. Bieri, E. Heilbronner, E. Kloster-Jensen, A. Schmelzer, J. Wirz: ibid. 57, 1265 (1974)CrossRefGoogle Scholar
  180. 178.
    R. W. Strozier, P. Caramella, K. N. Houk: J. Am. Chem. Soc. 101, 1340 (1979)CrossRefGoogle Scholar
  181. 179.
    N. G. Rondan, L. N. Domelsmith, K. N. Houk, A. T. Bowne, R. H. Levin: Tetrahedron Lett. 1979, 3237Google Scholar
  182. 180.
    D. M. Hoffman, R. Hoffmann, C. R. Fisel: J. Am. Chem. Soc. 104, 3858 (1982)CrossRefGoogle Scholar
  183. 181.
    P. Carlier, J. E. Dubois, P. Masclet, G. Mouvier: J. Electron Spectrosc. 7, 55 (1975)CrossRefGoogle Scholar
  184. 182.
    A. Krebs, W. Rüger: unpublished resultsGoogle Scholar
  185. 183.
    U. Höpfner: Diplom Thesis, Heidelberg 1976Google Scholar
  186. 184.
    H. Meier, H. Petersen: Synthesis 1978, 596Google Scholar
  187. 185.
    H. Meier, H. Gugel, H. Kolshorn: Z. Naturforsch. 31b, 1270 (1976)Google Scholar
  188. 186.
    H. N. C. Wong, F. Sondheimer: Tetrahedron 37, 99 (1981)CrossRefGoogle Scholar
  189. 187.
    R. M. Lynden-Bell, N. Sheppard: Proc. Roy. Soc. (London) A 269, 385 (1962)Google Scholar
  190. 188.
    D. M. Graham, C. E. Holloway: Can. J. Chem. 41, 2114 (1963)Google Scholar
  191. 189.
    J. Ulmen: Ph.D. Thesis, Köln 1973Google Scholar
  192. 190.
    O. L. Chapman, C.-C. Chang, J. Kolc, N. R. Rosenquist, H. Tomioka: J. Am. Chem. Soc. 97, 6586 (1975)CrossRefGoogle Scholar
  193. 191.
    A. T. Blomquist, R. E. Burge, jr., L. H. Liu, J. C. Bohrer, A. C. Sucsy, J. Kleis: ibid. 73, 5510 (1951)CrossRefGoogle Scholar
  194. 192.
    L. J. Bellamy: Advances in Infrared Group Frequencies, 1st Ed., Methuen, London 1968, p. 21–26Google Scholar
  195. 193.
    G. Wittig, P. Fritze: Liebigs Ann. Chem. 712, 79 (1968)Google Scholar
  196. 194.
    H. Meier, J. Heiss, H. Suhr, Eu. Müller: Tetrahedron 24, 2307 (1968)CrossRefGoogle Scholar
  197. 195.
    V. Franzen, H.-I. Joschek: Liebigs Ann. Chem. 703, 90 (1967)Google Scholar
  198. 196.
    H. Kolshorn, H. Meier, Eu. Müller: Tetrahedron Lett. 1972, 1589Google Scholar
  199. 197.
    T. J. Katz, S. J. Lee: J. Am. Chem. Soc. 102, 422 (1980)CrossRefGoogle Scholar
  200. 198.
    H. Kimling, A. Krebs: Angew. Chem. 84, 952 (1972); Angew. Chem. Int. Ed. Engl. 11, 932 (1972)Google Scholar
  201. 199.
    A. Krebs, H. Kimling, R. Kemper: Liebigs Ann. Chem. 1978, 431Google Scholar
  202. 200.
    R. J. Böttcher, H. Röttele, G. Schröder, J. F. M. Oth: Tetrahedron Lett. 1968, 3935Google Scholar
  203. 201.
    P. Puster: Ph.D. Thesis, Heidelberg 1976Google Scholar
  204. 202.
    G. H. Schmid: Thiiranium and Thiirenium Ions, in: Topics in Sulfur Chemistry, Vol. 3, 101, Thieme-Verlag, Stuttgart 1977Google Scholar
  205. 203.
    A. Krebs, H. Colberg: unpublished resultsGoogle Scholar
  206. 204.
    A. Krebs, B. Jessel: unpublished resultsGoogle Scholar
  207. 205.
    T. Nozoe, Y. Kitahara: Proc. Japan Acad. 30, 204 (1954); C.A. 49, 13 200 (1955)Google Scholar
  208. 206.
    T. Toda: Bull. Chem. Soc. Japan 40, 588 (1967)Google Scholar
  209. 207.
    T. Yamatani, M. Yasunami, K. Takase: Tetrahedron Lett. 1970, 1725Google Scholar
  210. 208.
    H. Colberg: Ph.D. Thesis, Hamburg 1980Google Scholar
  211. 209.
    A. Krebs, W. Rüger: unpublished resultsGoogle Scholar
  212. 210.
    A. Krebs, H. Colberg: unpublished resultsGoogle Scholar
  213. 211.
    N. J. Turro, V. Ramamurthy, K.-C. Liu, A. Krebs, R. Kemper: J. Am. Chem. Soc. 98, 6758 (1976)CrossRefGoogle Scholar
  214. 212.
    A. Krebs, H. Colberg: Chem. Ber. 113, 2007 (1980)Google Scholar
  215. 213.
    W. Spang, M. Hanack: ibid. 113, 2025 (1980)Google Scholar
  216. 214.
    G. Wittig, J. J. Hutchison: Liebigs Ann. Chem. 741, 79 (1970)Google Scholar
  217. 215.
    A. Krebs, H. Kimling: Angew. Chem. 83, 401 (1971); Angew. Chem. Int. Ed. Engl. 10, 409 (1971)Google Scholar
  218. 216.
    Y. Tjung: Ph.D. Thesis, Heidelberg 1975Google Scholar
  219. 217.
    K. H. Klaska, H. Colberg: unpublished resultsGoogle Scholar
  220. 218.
    A. Krebs, H. Colberg, U. Höpfner, H. Kimling, J. Odenthal: Heterocycles 12, 1153 (1979)Google Scholar
  221. 219.
    A. Krebs, K. Schütz: unpublished resultsGoogle Scholar
  222. 220.
    W. Tochtermann, P. Rösner: Tetrahedron Lett. 1980, 4905Google Scholar
  223. 221.
    W. Tochtermann, P. Rösner: Chem. Ber. 114, 3725 (1981)Google Scholar
  224. 222.
    J. Liebe, C. Wolff, W. Tochtermann: Tetrahedron Lett. 1982, 171Google Scholar
  225. 223.
    H. Dürr, B. Weiss: Angew. Chem. 87, 674 (1975); Angew. Chem. Int. Ed. Engl. 14, 646 (1975)Google Scholar
  226. 224.
    H. Dürr, A. C. Ranade, I. Halberstadt: Synthesis 1974, 878Google Scholar
  227. 225.
    K. Hafner, H. Diehl, H. U. Süss: Angew. Chem. 88, 121 (1976); Angew. Chem. Int. Ed. Engl. 15, 104 (1976)Google Scholar
  228. 226.
    G. Märkl, K. H. Heier: Tetrahedron Lett. 1974, 4369Google Scholar
  229. 227.
    T. Hosokawa, I. Moritani, S. Nishioka: ibid. 1969, 3833Google Scholar
  230. 228.
    W.-S. Lee, H. H. Brintzinger: J. Organometal. Chem. 127, 87 (1977)CrossRefGoogle Scholar
  231. 229.
    K. W. Lienert: Ph.D. Thesis, Hamburg 1981Google Scholar
  232. 230.
    J. Wilke: Ph.D. Thesis, Hamburg 1982Google Scholar
  233. 231.
    G. B. Robertson, P. O. Whimp: ibid. 97, 1051 (1975)Google Scholar

Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  1. 1.Institut für Organische Chemie und BiochemieUniversität HamburgHamburgFRG

Personalised recommendations