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Intramolecular Interaction in The Chemical Behavior of Carbon-Functional Organosilicon Compounds

  • Josef Pola
Part of the Modern Inorganic Chemistry book series (MICE)

Abstract

In many respects the unusual behavior of carbon-functional organosilicon compounds, i.e., compounds in which silicon is bonded to an sp3 hybridized carbon of an organic framework containing a functional group, Si---(C)n---functional group [functional group = a group bonded to the (C)n framework by an atom other than a formally neutral sp3 carbon] is associated with a greater atomic volume, a lower electronegativity, and more polarizable bonds of silicon compared to carbon (Chapter 4, Section 4.4). The greater atomic volume of silicon makes steric shielding less significant; in silacyclic compounds the greater atomic volume adds conformational effects that change torsional angles and transannular repulsions between non-bonded substituents of the ring. The lower electronegativity of silicon in trialkylsilyl substituted compounds creates a negative charge on the adjacent carbon, and the inductive mechanism provides the following charge distribution in a silyl-alkyl framework.

Keywords

Nucleophilic Attack Proton Affinity Intramolecular Interaction Alkyl Halide Nauk USSR 
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.

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References

  1. 1.
    Sommer L.H., Whitmore F.C. : J. Amer. Chem. Soc. 68, 485 (1946).Google Scholar
  2. 2.
    Sommer L.H., Baughman G.A. : J. Amer. Chem. Soc. 83, 3346 (1961).Google Scholar
  3. 3.
    Fleming I.: Chem. Ind. 1975, 449.Google Scholar
  4. 4.
    Eisch J.J., Trainor J.T.: J. Org. Chem. 28, 2870 (1963).Google Scholar
  5. 5.
    Litvinova O.V., Baukov Yu. I., Lutsenko I.F.: Dokl. Akad. Nauk USSR, 173, 578 (1967).Google Scholar
  6. 6.
    Ponomarev V.V., Golubcov S.A., Andrianov K.A., Kondrashova G.N.: Izv. Akad. Nauk USSR, Ser. Khim. 1969, 1545.Google Scholar
  7. 7.
    Davidson P.J., Lappert M.F., Pearce R.: Acc. Chem. Res. 7, 209 (1974).Google Scholar
  8. 8.
    Cundy C.S., Lappert M. F., Pearce R.: J. Organometal. Chem. 59, 161 (1973).Google Scholar
  9. 9.
    Eaborn C., Happer D.A.R., Safa K.D., Walton D.R.M.: J. Organometal. Chem. 157, C50 (1978).Google Scholar
  10. 10.
    Dua S.S., Eaborn C., Happer D.A.R., Hopper S.P., Safa K.D., Walton D.R.M.: J. Organometal. Chem. 178, 75 (1979).Google Scholar
  11. 11.
    Eaborn C., Retta N., Smith J.D.: J. Organometal. Chem. 190, 101 (1980).Google Scholar
  12. 12.
    Cook M.A., Eaborn C., Jukes A.E., Walton D.R.M.: J. Organometal. Chem. 24, 529 (1970).Google Scholar
  13. 13.
    Eaborn C., Eidenschink R., Jackson P.M., Walton D.R.M.: J. Organometal. Chem. 101, C 40 (1975).Google Scholar
  14. 14.
    Bourne A.J., Jarvie A.W.P., Holt A.: J. Chem. Soc. C, 1970, 1740.Google Scholar
  15. 15.
    Petrov A.D., Egorov Yu.P., Mironov V.F., Nikiskhin G.I., Bugorkova A.A.: Izv. Akad. Nauk USSR, Ser. Khim. 1956, 50.Google Scholar
  16. 16.
    Bugorkova A.A., Mironov V.F., Petrov A.D.: Izv. Akad. Nauk USSR, Ser. Khim. 1960, 474.Google Scholar
  17. 17.
    Ponomarev V.V., Golubcov S.A., Andrianov K.A., Chuprova E.A.: Izv. Akad. Nauk USSR, Ser. Khim. 1969, 1551.Google Scholar
  18. 18.
    Mironov V.F.: Izv. Akad. Nauk USSR, Ser. Khim. 1959, 1862.Google Scholar
  19. 19.
    Sommer L.H., Tyler L.J., Whitmore F.C.: J. Amer. Chem. Soc. 70, 2872 (1948).Google Scholar
  20. 20.
    Carsson E.: Trans. Chabmer. Univ. Technol. Gothenburg 115, 25 (1951).Google Scholar
  21. 21.
    Sakurai H., Hosomi A., Kumada M.: J. Org. Chem. 34, 1764 (1969).Google Scholar
  22. 22.
    Martin M.M., Gleicher G.J.: J. Amer. Chem. Soc. 86, 233, 238, 242 (1964).Google Scholar
  23. 23.
    Jarvie A.W.P., Rowley R.J.: J. Chem. Soc. B, 1971, 2439.Google Scholar
  24. 24.
    Cudlin J., Chvalovský V.: Coll. Czech. Chem. Commun. 27, 1658 (1962).Google Scholar
  25. 25.
    Dyakonov I.A., Golodnikov G.V., Repinskaya I.B.: Zh. Obshch. Khim. 35, 2181 (1965).Google Scholar
  26. 26.
    Dyakonov I.A., Repinskaya I.B., Golodnikov G.V.: Zh. Obshch. Khim. 36, 949 (1966).Google Scholar
  27. 27.
    Kirmse W.: Angew. Chem. 14, 678 (1962).Google Scholar
  28. 28.
    Chernyshev E.A.: Izv. Akad. Nauk USSR, Ser. Khim. 1960, 80.Google Scholar
  29. 29.
    Topchiev A.V., Nametkin N.S., Durgaryan S.G.: Zh. Obshch. Khim. 1960, 927.Google Scholar
  30. 30.
    Eaborn C., Emokpae T.A., Sidorov V.I., Taylor R.: J. Chem. Soc. Perkin II, 1974, 1454.Google Scholar
  31. 31.
    Bailey F.P., Taylor R.: J. Chem. Soc. B, 1971, 1446.Google Scholar
  32. 32.
    Bott R.W., Eaborn C., Leyshon K.: J. Chem. Soc. 1964, 1971.Google Scholar
  33. 33.
    Walton D.R.M.: J. Organometal. Chem. 3, 438 (1965).Google Scholar
  34. 34.
    Bassindale A.R., Eaborn C., Walton D.R.M., Young D.J.: J. Organometal. Chem. 20, 49 (1969).Google Scholar
  35. 35.
    Chernyshev E.A., Dolgaya M.E., Petrov A.D.: Izv. Akad. Nauk USSR, Ser. Khim. 1960, 1424.Google Scholar
  36. 36.
    Chernyshev E.A., Tolstikova N.G.: Izv. Akad. Nauk USSR, Ser. Khim. 1960, 1595.Google Scholar
  37. 37.
    Chernyshev E.A., Klyukina E.N., Petrov A.D.: Izv. Akad. Nauk USSR, Ser. Khim. 1960, 1601.Google Scholar
  38. 38.
    Eaborn C.: J. Chem. Soc. 1956, 4858.Google Scholar
  39. 39.
    Traylor T.G., Hanstein W., Berwin H.J., Clinton N.A., Brown R.S.: J. Amer. Chem. Soc. 93, 5715 (1971).Google Scholar
  40. 40.
    Hanstein W., Berwin H.J., Traylor T.G.: J. Amer. Chem. Soc. 92, 829 (1970).Google Scholar
  41. 41.
    Eaborn C., Parker S.H.: J. Chem. Soc. 1954, 939.Google Scholar
  42. 42.
    Cook M.A., Eaborn C., Walton D.R.M.: J. Organometal. Chem. 24, 293 (1970).Google Scholar
  43. 43.
    Benkeser R.A., Bennett E.W.: J. Amer. Chem. Soc. 80, 5414 (1958).Google Scholar
  44. 44.
    Sommer L.H., Gold J.R., Goldberg G.M., Marans N.S.: J. Amer. Chem. Soc. 71, 1509 (1949).Google Scholar
  45. 45.
    Rijkens F., Jansen M.J., Drenth W., Van Denkerk G.J.M.: J. Organometal. Chem. 2, 347 (1964).Google Scholar
  46. 46.
    Sommer L.H., Rockett J.: J. Amer. Chem. Soc. 73, 5130 (1951).Google Scholar
  47. 47.
    Voronkov M.G., Kashik T.V., Lukevics E.Y., Deriglazova E.S., Pestunovich A.E., Moskovich R.Y.: Zh. Obshch. Khim. 44, 778 (1974).Google Scholar
  48. 48.
    Voronkov M.G., Kashik T.V., Deriglazova E.S., Lukevics E.Y., Pestunovich A.E., Sturkovich R.Y.: Zh. Obshch. Khim. 46, 1522 (1976).Google Scholar
  49. 49.
    Voronkov M.G., Kashik T.V., Lukevics E.Y., Deriglazova E.S., Pestunovich A.E.: Zh. Obshch. Khim. 45, 2200 (1975).Google Scholar
  50. 50.
    Andrianov K.A., Kopylov V.M., Chernyshev A.I., Andreva S.V., Shragin I.S.: Zh. Obshch. Khim. 45, 351 (1975).Google Scholar
  51. 51.
    Fialová V., Bazant V., Chvalovský V.: Coll. Czech. Chem. Commun. 38, 3837 (1973).Google Scholar
  52. 52.
    Lukevics E.Y., Voronkov M.G., Shestakov E.E., Pestunovich A.E.: Zh. Obshch. Khim. 41, 2218 (1971).Google Scholar
  53. 53.
    Shea K.J., Gobeille R., Bramblett J., Thompson E.: J. Amer. Chem. Soc. 100, 1611 (1978).Google Scholar
  54. 54.
    Egorochkin A.N., Skobeleva S.E., Sevastyanova E.I., Kosolapova I.G., Sheludyakov V.D., Rodionov E.S., Kirilin A.D.: Zh. Obshch. Khim. 46, 1795 (1976).Google Scholar
  55. 55.
    Pola J., Bazant V., Chvalovský V.: Coll. Czech. Chem. Commun. 37, 3885 (1972).Google Scholar
  56. 56.
    Jarvie A.W.P., Holt A., Thompson J.: J. Chem. Soc. B 1969, 852.Google Scholar
  57. 57.
    Brownbridge P., Fleming I., Pearce A., Warren S.: J. Chem. Soc., Chem. Commun. 1976, 751.Google Scholar
  58. 58.
    Davidson A.H., Fleming I., Grayson J.I., Pearce A., Snowden R.L., Warren S.: J. Chem. Soc. Perkin I, 1977, 550.Google Scholar
  59. 59.
    Fleming I., Patel S.K.: Tetrahedron Lett. 22, 2321 (1981).Google Scholar
  60. 60.
    Eaborn C., Mahmoud F.M.S.: J. Organometal. Chem. 209, 13 (1981).Google Scholar
  61. 61.
    Davis D.D., Black R.H.: J. Organometal. Chem. 82, C 30 (1974).Google Scholar
  62. 62.
    Washburne S.S., Chawla R.R.: J. Organometal. Chem. 133, 7 (1977).Google Scholar
  63. 63.
    Heck R., Prelog V.: Helv. Chim. Acta 38, 1541 (1955).Google Scholar
  64. 64.
    Pola J., Chvalovský V.: Coll. Czech. Chem. Commun. 39, 2247 (1974).Google Scholar
  65. 65.
    Pola J., Chvalovský V.: Coll. Czech. Chem. Commun. 39, 2637 (1974).Google Scholar
  66. 66.
    Shostakovskii M.F., Shikhiev I.A., Komarov N.V.: Izv. Akad. Nauk USSR, Ser. Khim. 1956, 1493.Google Scholar
  67. 67.
    Shostakovskii M.F., Vlasova N.N., Cyganskaya I.I., Emelyanov I.F.: Zh. Obshch. Khim. 40, 1897 (1978).Google Scholar
  68. 68.
    Pola J., Bellama J.M., Chvalovský V.: Coll. Czech. Chem. Commun. 39, 3705 (1974).Google Scholar
  69. 69.
    Badger R.M., Bauer J.M.: J. Chem. Phys. 5, 839 (1937).Google Scholar
  70. 70.
    Drago R.S.: Structure and Bonding 15, 73 (1973).Google Scholar
  71. 71.
    Pola J., Jakoubkova M., Chvalovský V.: Coll. Czech. Chem. Commun. 43, 760 (1978).Google Scholar
  72. 72.
    Pola J., Jakoubkova M., Chvalovský V.: Coll. Czech. Chem. Commun. 40, 2063 (1975) and references therein.Google Scholar
  73. 73.
    Pola J., Chvalovský V.: Coll. Czech. Chem. Commun. 38, 1674 (1973).Google Scholar
  74. 74.
    Bellama J.M., Davison J.B.: Inorg. Chem. 14, 3119 (1975).Google Scholar
  75. 75.
    Bellama J.M., Harmon L.A.: Inorg. Chem. 17, 482 (1978).Google Scholar
  76. 76.
    Bellama J.M., Gerchman L.L.: Inorg. Chem. 14, 161 (1975).Google Scholar
  77. 77.
    Huheey J.E.: J. Phys. Chem. 69, 3284 (1965).Google Scholar
  78. 78.
    Wang J.T., Van Dyke C.H.: Inorg. Chem. 6, 1741 (1967).Google Scholar
  79. 79.
    Gibbon G.A., Wang J.T., Van Dyke C.H.: Unpublished results, cited in ref. 76.Google Scholar
  80. 80.
    Pola J., Chvalovský V.: Coll. Czech. Chem. Commun. 45, 861 (1980).Google Scholar
  81. 81.
    Hetflejš J., Svoboda L., Jakoubková M., Chvalovský V.: Coll. Czech. Chem. Commun. 38, 717 (1973).Google Scholar
  82. 82.
    Shostakovskii M.F., Komarov N.V., Vlasova N.N.: Zh. Obshch. Khim. 37, 1151 (1967).Google Scholar
  83. 83.
    Shostakovskii M.F., Komarov N.V., Vlasova N.N., Rinkus G.A.: Zh. Obshch. Khim. 36, 904 (1966).Google Scholar
  84. 84.
    Ingold C.K.: Structure and Mechanism in Organic Chemistry, Second Ed., Cornell University Press, Ithaca 1969, Chapter 7.Google Scholar
  85. 85.
    Eaborn C.: Organosilicon Compounds, Butterworths, London 1960, p. 433.Google Scholar
  86. 86.
    Cook M.A., Eaborn C., Walton D.R.M.: J. Organometal. Chem. 29, 389 (1971).Google Scholar
  87. 87.
    Cartledge F.K., Jones J.P.: Tetrahedron Lett. 1971, 2193.Google Scholar
  88. 88.
    Cartledge F.K., Jones J.P.: J. Organoraetal. Chem. 67, 379 (1974).Google Scholar
  89. 89.
    Cook M.A., Eaborn C., Walton D.R.M.: J. Organoraetal. Chem. 24, 301 (1970).Google Scholar
  90. 90.
    Eaborn C., Jeffrey J.C.: J. Chera. Soc. 1954, 4266.Google Scholar
  91. 91.
    Cooper G.D., Prober M.: J. Amer. Chem. Soc. 76, 3943 (1954).Google Scholar
  92. 92.
    Mironov V.F., Pogonkina N.A.: Izv. Akad. Nauk USSR, Ser. Khim. 1957, 1199.Google Scholar
  93. 93.
    Huang C.T., Wang P.J.: Hua Hsüeh Hsüeh Pao 25, 330 (1959), Chem. Abstr. 54, 16375 d (1960).Google Scholar
  94. 94.
    Eaborn C., Jeffrey C.: J. Chem. Soc. 1957, 137.Google Scholar
  95. 95.
    Whitmore F.C., Sommer L.H.: J. Amer. Chem. Soc. 68, 481 (1946).Google Scholar
  96. 96.
    Miller V.B., Neiman M.B., Savickii A.V., Mironov V.F.: Dokl. Akad. Nauk USSR, 121, 495 (1955).Google Scholar
  97. 97.
    Smith R.P., Eyring H.: J. Amer. Chem. Soc. 74, 229 (1952).Google Scholar
  98. 98.
    Boak D.S., Gowenlock B.G.: J. Organometal. Chem. 29, 385 (1971).Google Scholar
  99. 99.
    Včelák J., Roman L., Chvalovský V.: Coll. Czech. Chem. Commun. 41, 2708 (1976).Google Scholar
  100. 100.
    Ref. 83, pp 204–206.Google Scholar
  101. 101.
    Steward O.W., Pierce O.R.: J. Amer. Chem. Soc. 83, 4932 (1961).Google Scholar
  102. 102.
    Joesten M.D., Shaad L.J.: Hydrogen Bonding, Chap. 4, M. Dekker. New York 1974.Google Scholar
  103. 103.
    Badger R.M., Bauer J.M.: J. Chem. Phys. 5, 835 (1937).Google Scholar
  104. 104.
    Drago R.S.: Structure and Bonding 15, 73 (1973).Google Scholar
  105. 105.
    Pola J., Jakoubkova M., Chvalovský V.: Coll. Czech. Chem. Commun. 43, 753 (1978).Google Scholar
  106. 106.
    Pola J., Chvalovský V.: Coll. Czech. Chem. Commun. 43, 3192 (1978).Google Scholar
  107. 107.
    Zhdanov Y.A., Minkin V.I.: Korrelacionnyi Analiz v Organischeskoi Khimii, Izd. Rostov. Univ., Rostov 1966.Google Scholar
  108. 108.
    Voronkov M.G., Feshin V.P., Mironov V.F., Mikhailants S.A., Gar T.K.: Zh. Obshch. Khim. 41, 2211 (1971).Google Scholar
  109. 109.
    Pola J., Chvalovský V.: Coll. Czech. Chem. Commun. 42, 3581 (1977).Google Scholar
  110. 110.
    Chernyshev E.A., Dolgaya M.E.: Zh. Obshch. Khim. 29, 1850 (1959).Google Scholar
  111. 111.
    Abel E.W., Dunster M.O., Waters A.: J. Organometal. Chem. 49, 287 (1973).Google Scholar
  112. 112.
    Larrabee R.B.: J. Organometal. Chem. 74, 313 (1974).Google Scholar
  113. 113.
    Asche A.J.: J. Amer. Chem. Soc. 92, 1233 (1970).Google Scholar
  114. 114.
    Fritz H.P., Kreiter C.G.: J. Organometal. Chem. 4, 313 (1965).Google Scholar
  115. 115.
    Calderon J.L., Cotton F.A., Legzdins P.: J. Amer. Chem. Soc. 91, 2528 (1969).Google Scholar
  116. 116.
    Sergeyev N.M., Avramenko G.I., Ustynuk Y.A.: J. Organometal. Chem. 22, 79 (1970).Google Scholar
  117. 117.
    Egger K.W., James T.L.: J. Organometal. Chem. 26, 335 (1971).Google Scholar
  118. 118.
    Sergeyev N.M., Avramenko G.I., Kisin A.V., Korenvesky U.A., Ustynuk Y.A.: J. Organometal. Chem. 32, 55, 77 (1971).Google Scholar
  119. 119.
    Luzikov Y.N., Sergeyev N.M., Ustynuk Y.A.: J. Organometal. Chem 65, 303 (1974).Google Scholar
  120. 120.
    Boche G., Heidenhaim F.: J. Organometal. Chem. 121, C 49 (1976).Google Scholar
  121. 121.
    Mironov V.F., Sherbinin V.V., Viktorov N.A., Sheludyakov V.D.: Zh. Obshch. Khim. 45, 1908 (1975).Google Scholar
  122. 122.
    Asche A.J.: J. Amer. Chem. Soc. 95, 818 (1973).Google Scholar
  123. 123.
    Cunico R.F., Lee H.M.: J. Amer. Chem. Soc. 99, 7613 (1977).Google Scholar
  124. 124.
    Reetz M.T.: Tetrahedron 29, 2189 (1973).Google Scholar
  125. 125.
    Nametkin N.S., Grushevenko I.A., Perchenko V.N., Kamneva G.L.: Dokl. Akad. Nauk USSR 207, 865 (1972).Google Scholar
  126. 126.
    Brook A.G., Duff J.M.: J. Amer. Chem. Soc. 96, 4692 (1974).Google Scholar
  127. 127.
    Bassindale A.R., Brook A.G., Jones D.F., Stewart J.A.G.: J. Organometal. Chem. 152, C 25 (1978).Google Scholar
  128. 128.
    Kaufmann K.D., Rühlmann K.: Z. Chem. 8, 262 (1968).Google Scholar
  129. 129.
    Brook A.G.: Acc. Chem. Res. 7, 77 (1974).Google Scholar
  130. 130.
    Gilman H., Wu T.C.: J. Amer. Chem. Soc. 75, 2935 (1953).Google Scholar
  131. 131.
    Brook A.G., Limburg W.W., MacRae D.M., Fieldhouse S.A.: J. Amer. Chem. Soc. 89, 704 (1967).Google Scholar
  132. 132.
    Brook A.G., Schwartz N.V.: J. Org. Chem. 27, 2311 (1962).Google Scholar
  133. 133.
    Brook A.G., Fieldhouse S.A.: J. Organometal. Chem. 10, 235 (1967).Google Scholar
  134. 134.
    Bassindale A.R., Brook A.G., Chen P., Lennon J.: J. Organometal. Chem. 94, C 21 (1975).Google Scholar
  135. 135.
    Wilt J.W., Kolewe O., Kraemer J.F.: J. Amer. Chem. Soc. 91, 2624 (1969).Google Scholar
  136. 136.
    Reetz M.T.: Angew. Chem., Int. Ed. Engl. 13, 402 (1974).Google Scholar
  137. 137.
    Atwell W.H., Weyenberg D.R., Uhlmann J.G.: J. Amer. Chem. Soc. 91, 2024 (1969).Google Scholar
  138. 138.
    Haszeldine R.N., Rogers D.J., Tipping A.E.: J. Organometal. Chem. 54, C 5 (1973).Google Scholar
  139. 139.
    Brook A.G., Jones P.F. : J. Chem. Soc, Chem. Commun. 1969, 1325.Google Scholar
  140. 140.
    Wright A., West R.: J. Amer. Chem. Soc. 96, 3222 (1974).Google Scholar
  141. 141.
    Fishwick G., Haszeldine R.N., Parkinson C., Robinson P.J., Simmons R.F.: J. Chem. Soc, Chem. Commun. 1965, 382.Google Scholar
  142. 142.
    Haszeldine R.N., Young J.C.: Proc Chem. Soc. 1959, 394.Google Scholar
  143. 143.
    Weber W.P., Felix R.A., Willard A.K., Koenig K.E.: Tetrahedron Lett. 1971, 4701.Google Scholar
  144. 144.
    Bevan W.I., Haszeldine R.N., Middleton J., Tipping A.E.: J. Organometal. Chem. 23, C 17 (1970).Google Scholar
  145. 145.
    Whitmore F.C., Sommer L.H., Gold J.: J. Amer. Chem. Soc. 69, 1976 (1947).Google Scholar
  146. 146.
    O’Brien D.H., Hairston T.J.: Organometal. Chem. Rev. A 7, 132 (1971).Google Scholar
  147. 147.
    Bott R.W., Eaborn C., Rushton B.M.: J. Organometal. Chem. 3, 455 (1965).Google Scholar
  148. 148.
    Bellama J.M., MacDiarmid A.G.: J. Organometal. Chem. 18, 275 (1969).Google Scholar
  149. 149.
    Voronkov M.G., Kirpichenko S.V., Keiko V.V., Pestunovich V.A., Tsetlina E.O., Chvalovský V., Vcelak J.: Izv. Akad. Nauk USSR, Ser. Khim. 1975, 2052.Google Scholar
  150. 150.
    Corey J.Y., Chang V.H.T.: J. Organometal. Chem. 174, C 15 (1979).Google Scholar
  151. 151.
    Slutsky J., Kwart H.: J. Amer. Chem. Soc. 95, 8678 (1973).Google Scholar
  152. 152.
    Ishikawa M., Sugisawa H., Fábry L., Kumada M.: J. Organometal. Chem. 161, 299 (1978).Google Scholar
  153. 153.
    Belavin I.Y., Fedoseeva N.A., Baukov Y.I., Lutsenko I.F.: Zh. Obshch. Khim. 43, 433 (1973).Google Scholar
  154. 154.
    Brook A.G., MacRae D.M., Limburg W.W.: J. Amer. Chem. Soc. 89, 5493 (1967).Google Scholar
  155. 155.
    Kwart H., Barnette W.E.: J. Amer. Chem. Soc. 99, 614 (1977).Google Scholar
  156. 156.
    Larson G.L., Fernandez Y.V.: J. Organometal. Chem. 86, 193 (1975).Google Scholar
  157. 157.
    Brook A.G., Anderson D.F., Duff J.M.: J. Amer. Chem. Soc. 90, 3876 (1968).Google Scholar
  158. 158.
    Brook A.G., Duff J.M., Anderson D.G.: J. Amer. Chem. Soc. 92, 7567 (1970).Google Scholar
  159. 159.
    Brook A.G., Anderson D.G.: Can. J. Chem. 46, 2115 (1968).Google Scholar
  160. 160.
    Vedejs E., Mullins M.: Tetrahedron Lett. 1975, 2017.Google Scholar
  161. 161.
    Nesmeyanov A.N.: J. Organometal. Chem. 100, 161 (1975).Google Scholar
  162. 162.
    Lutsenko I.F., Baukov Y.I., Kostyuk A.S., Savelyeva N.I., Krysina V.K.: J. Organometal. Chem. 17, 241 (1969).Google Scholar
  163. 163.
    Itoh K., Kato S., Ishii Y.: J. Organometal. Chem. 34, 293 (1973).Google Scholar
  164. 164.
    Canavan A.E., Eaborn C.: J. Chem. Soc. 1962, 592.Google Scholar
  165. 165.
    Saveleva N.I., Kostyuk A.S., Baukov Y.I., Lutsenko I.F.: Zh. Obshch. Khim. 41, 485 (1971).Google Scholar
  166. 166.
    Musker W.K., Larson G.L.: J. Amer. Chem. Soc. 91, 514 (1969).Google Scholar
  167. 167.
    Gilman H., Tomasi R.A.: J. Org. Chem. 27, 3647 (1962).Google Scholar
  168. 168.
    Connor J.A., Jones E.M.: J. Organometal. Chem. 60, 77 (1973).Google Scholar
  169. 169.
    Peterson D.J.: J. Org. Chem. 33, 780 (1968).Google Scholar
  170. 170.
    Chan T.H., Chang E., Vinokur E.: Tetrahedron Lett. 1970, 1137.Google Scholar
  171. 171.
    Matsuda I., Izumi Y.: Tetrahedron Lett. 22, 1805 (1981).Google Scholar
  172. 172.
    Seyferth D., Lefferts J.L., Lambert R.L.: J. Organometal. Chem. 142, 39 (1977).Google Scholar
  173. 173.
    Seebach D., Gröbel B.T., Beck A.K., Braun M., Geiss K.H.: Angew. Chem., Int. Ed. Engl. 11, 443 (1972).Google Scholar
  174. 174.
    Carey F.A., Hernandez O.: J. Org. Chem. 38, 2670 (1973).Google Scholar
  175. 175.
    Shimoji K., Taguchi H., Oshima K., Aymamoto H., Nozaki H.: J. Amer. Chem. Soc. 96, 1620 (1974).Google Scholar
  176. 176.
    Haszeldine R.N., Robinson P.J., Simmons R.F.: J. Chem. Soc. 1964, 1890.Google Scholar
  177. 177.
    Graham D., Haszeldine R.N., Robinson P.J.: J. Chem. Soc. B 1969, 652.Google Scholar
  178. 178.
    Graham D., Haszeldine R.N., Robinson P.J.: J. Chem. Soc. B 1971, 611.Google Scholar
  179. 179.
    Bell T.N., Berkley R., Platt A.E., Sherwood A.G.: Canad. J. Chem. 52, 3158 (1974).Google Scholar
  180. 180.
    Fishwick G., Haszeldine R.N., Robinson P.J., Simmons R.F.: J. Chem. Soc. B 1970, 1236.Google Scholar
  181. 181.
    Bell T.N., Haszeldine R.N., Newlands M.J., Plumb J.B. : J. Chem. Soc. 1965, 2107.Google Scholar
  182. 182.
    Davidson I.M.T., Eaborn C., Lilly M.N.: J. Chem. Soc. 1964, 2624, 2630.Google Scholar
  183. 183.
    Davidson I.M.T.: J. Chem. Soc. 1965, 5481.Google Scholar
  184. 184.
    Davidson I.M.T., Jones M.R., Pett C.: J. Chem. Soc. B 1967, 937.Google Scholar
  185. 185.
    Ponomarev V.V., Shapatin A.S., Golubcov S.A.: Zh. Obshch. Khim. 36, 364 (1966).Google Scholar
  186. 186.
    Sato Y., Ban Y., Shirai H.: J. Organometal. Chem. 113, 115 (1976).Google Scholar
  187. 187.
    Sato Y., Toyooka T., Aoyama T., Shirai H.: J. Org. Chem. 41, 3559 (1976).Google Scholar
  188. 188.
    Sato Y., Ban Y., Aoyama T., Shirai H.: J. Organometal. Chem. 41, 1962 (1976).Google Scholar
  189. 189.
    Gilman H., Tomasi R.A.: J. Amer. Chem. Soc. 81, 137 (1959).Google Scholar
  190. 190.
    Maercker A., Eckers M., Passlack M.: J. Organometal. Chem. 186, 193 (1980).Google Scholar
  191. 191.
    Dolzine T.W., Hovland A.K., Oliver J.P.: J. Organometal. Chem. 65, C 1 (1974).Google Scholar
  192. 192.
    Scherer O.J., Schnabl G.: J. Organometal. Chem. 52, C 18 (1973).Google Scholar
  193. 193.
    Belyakova Z.V., Bochkarev V.N., Golubcov S.A., Belikova Z.V., Yamova M.S., Ainshtein A.A., Baranova G.G., Efremova L.A., Popkov K.K.: Zh. Obshch. Khim. 42, 858 (1972).Google Scholar
  194. 194.
    Bailey D.L.: U.S. Patent 2 888 454 (1959).Google Scholar
  195. 195.
    Andrianov K.A., Pakhomov V.I., Lapteva N.E.: Dokl. Akad. Nauk USSR, 151, 849 (1963).Google Scholar
  196. 196.
    Manuel G., Mazerolles P., Florence J.C.: J. Organometal. Chem. 30, 5 (1971).Google Scholar
  197. 197.
    Massol M., Barrau J., Satge J., Bouyssieres B.: J. Organometal. Chem. 80, 47 (1974).Google Scholar
  198. 198.
    Speier J.L., David M.P., Eynon B.A.: J. Org. Chem. 25, 1637 (1960).Google Scholar
  199. 199.
    Sommer L.H.: U.S. Patent 2 589 446 (1952).Google Scholar
  200. 200.
    Pola J., Bazant V., Chvalovský V.: Coll. Czech. Chem. Commun. 38, 1528 (1973).Google Scholar
  201. 201.
    Grignon-Dubois M., Dunogues J., Duffant N., Calas R.: J. Organometal. Chem. 188, 311 (1980).Google Scholar
  202. 202.
    Tsuge O., Sone K., Urano S., Matsuda K.: J. Org. Chem. 47, 5171 (1982).Google Scholar
  203. 203.
    Bac N.V., Langlois Y.: J. Amer. Chem. Soc. 104, 7666 (1982).Google Scholar
  204. 204.
    Onan K.D., McPhail A.T., Yoder C.H., Hilliard R.W.: J. Chem. Soc, Chem. Commun. 1978, 209.Google Scholar
  205. 205.
    Hilliard R.W., Ryan C.M., Yoder C.H.: J. Organometal. Chem. 153, 369 (1978).Google Scholar
  206. 206.
    Weber W.P., Felix R.A., Willard A.K., Boettger H.G.: J. Org. Chem. 36, 4060 (1971).Google Scholar
  207. 207.
    Novikov S.N., Kazan E.G., Pravednikov A.N.: Zh. Obshch. Khira. 38, 402 (1968).Google Scholar
  208. 208.
    Mansuy D., Pusset J., Chottard J.C.: J. Organometal. Chem. 110, 139 (1976).Google Scholar
  209. 209.
    Wittenberg D., Gilman H.: J. Amer. Chem. Soc. 80, 2677 (1958) and references therein.Google Scholar
  210. 210.
    Casey C.P., Jones C.R., Tukada H.: J. Org. Chem. 46, 2089 (1981).Google Scholar
  211. 211.
    Zhdanov A.A., Pakhomov V.I., Arkhipov I.A.: Plast. Massy 1966, 19.Google Scholar
  212. 212.
    Simler W., Niederprüm H., Sattlegger H.: Chem. Ber. 99, 1368 (1966).Google Scholar
  213. 213.
    Saam J.C.: U.S. Patent 3 395 167 (1968).Google Scholar
  214. 214.
    Pola J., Jakoubková M., Chvalovský V.: Coll. Czech. Chem. Commun. 41, 374 (1976).Google Scholar
  215. 215.
    Weber W.P., Felix R.A., Willard A.K.: J. Amer. Chem. Soc. 92, 1420 (1970).Google Scholar
  216. 216.
    Weber W.P., Felix R.A., Wilard A.K., Boettger H.G.: J. Org. Chem. 36, 4060 (1971).Google Scholar
  217. 217.
    Benkeser R., Brumfield P.E.: J. Amer. Chem. Soc. 74, 253 (1952).Google Scholar
  218. 218.
    Nametkin N.S., Vdovin V.M., Pushevaya K.S.: Dokl. Akad. Nauk USSR 150, 562 (1963).Google Scholar
  219. 219.
    Duboudin F., Bourgeois G., Faucher A., Mazerolles P.: J. Organometal. Chem. 133, 29 (1977).Google Scholar

Copyright information

© Plenum Press, New York 1984

Authors and Affiliations

  • Josef Pola
    • 1
  1. 1.Institute of Chemical Process FundamentalsCzechoslovak Academy of SciencesPragueCzechoslovakia

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