Advertisement

Phase-transfer catalyzed reactions

  • Fernando Montanari
  • Dario Landini
  • Franco Rolla
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 101)

Keywords

Organic Phase Crown Ether Observe Rate Constant Quaternary Salt Phosphonium Salt 
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.

9 References

  1. 1.
    Parker, A. J.: Chem. Rev. 69, 1 (1969)Google Scholar
  2. 2.
    Pedersen, C. J.: J. Am. Chem. Soc. 89, 2495, 7017 (1967)Google Scholar
  3. 3.
    Pedersen, C. J., Frensdorff, H. K.: Angew. Chem., Int. Ed. Engl. 11, 16 (1972)Google Scholar
  4. 4.
    Dietrich, B., Lehn, J.-M., Sauvage, J. P.: Tetrahedron Lett. 1969, 2885, 2889Google Scholar
  5. 5.
    Lehn, J.-M.: Structure and Bonding 16, 1 (1973)Google Scholar
  6. 6.
    Makosza, M., Serafin, B.: Rocz. Chem. 39, 1223 (1965)Google Scholar
  7. 7.
    Makosza, M.: Pure Appl. Chem. 43, 439 (1975)Google Scholar
  8. 8.
    Brändström, A., Gustavii, K.: Acta Chem. Scand. 23, 1215 (1969)Google Scholar
  9. 9.
    Brändström, A.: Preparative Ion-Pair Extraction. Läkemedel: Apotekarsocieteten, AB Hässle 1974Google Scholar
  10. 10.
    Starks, C. M., Napier, D. R.: Ital. Patent 832, 967 (1968), Brit. Patent 1, 227, 144 (1971), French Patent 1, 573, 164 (1969); Chem. Abstr. 72, 115271 (1970)Google Scholar
  11. 11.
    Starks, C. M.: J. Am. Chem. Soc. 93, 195 (1971)Google Scholar
  12. 12.
    Starks, C. M., Owens, R. M.: J. Am. Chem. Soc. 95, 3613 (1973)Google Scholar
  13. 13.
    Jarousse, J.: C.R. Acad. Sci. Paris, Ser. C 232, 1424 (1951)Google Scholar
  14. 14.
    Germ. Offenl. 268, 621, to BASF (1913); Chem. Zentr. 1914, 310Google Scholar
  15. 15.
    Gibson, N. A., Hosking, J. W.: Aust. J. Chem. 18, 123 (1965)Google Scholar
  16. 16.
    Dockx, J.: Synthesis 1973, 441Google Scholar
  17. 17.
    Dehmlow, E. V.: Angew. Chem., Int. Ed. Engl. 13, 170 (1974)Google Scholar
  18. 18.
    Montanari, F.: Chim. Ind. (Milan) 57, 17 (1975)Google Scholar
  19. 19.
    Makosza, M.: Naked anions-phase transfer. In: Modern Synthetic Methods 1976. Scheffold, R. (ed.), pp. 7–100. Zürich: Schweizerischer Chemiker-Verband 1976Google Scholar
  20. 20.
    Dou, H. J.-M.: Chimie Actualités 1976, 41Google Scholar
  21. 21.
    Jones, R. A.: Aldrichimica Acta 9, 35 (1976)Google Scholar
  22. 22.
    Schacht, E.: Kontakte 1976, 3Google Scholar
  23. 23.
    Dehmlow, E. V.: Angew. Chem., Int. Ed. Engl. 16, 493 (1977)Google Scholar
  24. 24.
    Makosza, M.: Russ. Chem. Rev. 46, 1151 (1977)Google Scholar
  25. 25.
    Brändström, A.: Principles of phase-transfer catalysis by quaternary ammonium salts. In: Adv. Phys. Org. Chem., vol. 15, Fold, V. (ed.), pp. 267–330. New York: Academic Press 1977Google Scholar
  26. 26.
    Varughese, P.: J. Chem. Educ. 54, 666 (1977)Google Scholar
  27. 27.
    Jones, R. C. F.: Gen. Synth. Methods 1, 424 (1978)Google Scholar
  28. 28.
    McIntosh, J. M.: J. Chem. Educ. 55, 235 (1978)Google Scholar
  29. 29.
    Weber, W. P., Gokel, G. W.: J. Chem. Educ. 55, 350, 429 (1978)Google Scholar
  30. 30.
    Dou, H. J.-M.: Actual Chim. 1978, 7Google Scholar
  31. 31.
    Makosza, M.: Two-phase reactions in organic chemistry. In: Survey of Progress in Chemistry, vol. 9. New York: Academic Press 1979Google Scholar
  32. 32.
    Keller, V. E.: Compendium of phase-transfer reactions and related synthetic methods. Buchs: Fluka AG 1979Google Scholar
  33. 33.
    Dehmlow, E. V.: Chimia 34, 12 (1980)Google Scholar
  34. 34.
    D'Incan, E., Viout, P.: Techniques Ing. J-II92, 1 (1980)Google Scholar
  35. 35.
    Weber, W. P., Gokel, G. W.: Phase transfer catalysis in organic synthesis, Berlin-Heidelberg-New York: Springer-Verlag 1977Google Scholar
  36. 36.
    Starks, C. M., Liotta, C.: Phase transfer catalysis. Principles and techniques. New York: Academic Press 1978Google Scholar
  37. 37.
    Dehmlow, E. V., Dehmlow, S. S.: Phase transfer catalysis. Weinheim: Verlag Chemie 1980Google Scholar
  38. 38.
    Gokel, G. W., Durst, H. D.: Synthesis 1976, 168Google Scholar
  39. 39.
    Knipe, A. C.: J. Chem. Educ. 53, 618 (1976)Google Scholar
  40. 40.
    Izatt, R. M., Christensen, J. J.: Synthetic multidentate macrocyclic compounds. New York: Academic Press 1978Google Scholar
  41. 41.
    Lehn, J.-M.: Acc. Chem. Res. 11, 49 (1978)Google Scholar
  42. 42.
    Lehn, J.-M.: Pure Appl. Chem. 52, 2303 (1980)Google Scholar
  43. 43.
    Bradshaw, J. S., Stott, P. E.: Tetrahedron 36, 461 (1980)Google Scholar
  44. 44.
    Weber, E., Vögtle, F.: Kontakte 1977, 26Google Scholar
  45. 45.
    Weber, E., Vögtle, F.: Kontakte 1977, 48Google Scholar
  46. 46.
    Weber, E., Vögtle, F.: Kontakte 1978, 16Google Scholar
  47. 47.
    Vögtle, F., Weber, E., Elben, U.: Kontakte 1980, 36Google Scholar
  48. 48.
    Caubère, P.: Acc. Chem. Res. 7, 301 (1974)Google Scholar
  49. 49.
    Meyers, C. Y. et al.: New syntheses and reactions of organic compounds: reactions with carbon tetrachloride and other perhalomethanes in powdered potassium hydroxide-t-butyl alcohol. In: Catalysis in Organic Synthesis, pp. 197–278. New York: Academic Press 1977Google Scholar
  50. 50.
    Meyers, C. Y.: New reactions and syntheses of organic compounds. Reactions of sulfones with CCl4 and other perhalomethanes in KOH-t-BuOH. In: Topics in Organic Sulfur Chemistry. Tishler, M. (ed.), pp. 207–260. Ljubljiana: University Press 1978Google Scholar
  51. 51.
    Modin, R., Schill, G.: Acta Pharm. Suec. 4, 301 (1967)Google Scholar
  52. 52.
    Modin, R.: Acta Pharm. Suec. 9, 157 (1972), and references thereinGoogle Scholar
  53. 53.
    Gustavii, K.: Acta Pharm. Suec. 4, 233 (1967)Google Scholar
  54. 54.
    Gustavii, K., Schill, G.: Acta Pharm. Suec. 3, 241 (1966)Google Scholar
  55. 55.
    Ref. [37], p. 14Google Scholar
  56. 56.
    Gordon, J. E., Kutina, R. E.: J. Am. Chem. Soc. 99, 3903 (1977)Google Scholar
  57. 57.
    Dehmlow, E. V., Slopianka, M., Heider, J.: Tetrahedron Lett. 1977, 2361Google Scholar
  58. 58.
    Kheifets, V. L., Yakovleva, N. A., Krasil'schik, B. Ya.: Zh. Prikl. Khim. 46, 549 (1973); Chem. Abstr. 79, 10505 (1973)Google Scholar
  59. 59.
    Landini, D., Maia, A., Montanari, F.: J. Am. Chem. Soc. 100, 2796 (1978)Google Scholar
  60. 60.
    Landini, D., Maia, A., Montanari, F.: Nouv. J. Chim. 3, 575 (1979)Google Scholar
  61. 61.
    Landini, D., Maia, A., Montanari, F.: unpublished resultsGoogle Scholar
  62. 62.
    Makosza, M., Fedorynski, M.: Synth. Commun. 3, 305 (1973)Google Scholar
  63. 63.
    Agarwal, B. R., Diamond, R. M.: J. Phys. Chem. 67, 2785 (1963)Google Scholar
  64. 64.
    Freedman, H. H., Dubois, R. A.: Tetrahedron Lett. 1975, 3251Google Scholar
  65. 65.
    Antoine, J. P. et al.: Bull. Soc. Chim. Fr. 1980-II, 207Google Scholar
  66. 66.
    Herriott, A. W., Picker, D.: J. Am. Chem. Soc. 97, 2345 (1975)Google Scholar
  67. 67.
    Landini, D., Maia, A., Montanari, F.: J. Chem. Soc., Chem. Commun. 1977, 112Google Scholar
  68. 68.
    Landini, D. et al.: J. Chem. Soc., Chem. Commun. 1975, 950Google Scholar
  69. 69.
    Menger, F. N.: J. Am. Chem. Soc. 92, 5965 (1970)Google Scholar
  70. 70.
    Fendler, J. H., Fendler, E. J.: Catalysis in micellar and macromolecular systems. New York: Academic Press 1975Google Scholar
  71. 71.
    Horner, L., Gerhard, J.: Justus Liebigs Ann. Chem. 1980, 838Google Scholar
  72. 72.
    Ref. [36], p. 32Google Scholar
  73. 73.
    Uglestad, J., Ellingsen, T., Berge, A.: Acta Chem. Scand. 20, 1592 (1966)Google Scholar
  74. 74.
    Bhattacharyya, D. N. et al.: J. Phys. Chem. 69, 608 (1965)Google Scholar
  75. 75.
    Kraus, C. A.: J. Phys. Chem. 60, 129 (1956)Google Scholar
  76. 76.
    Davies, M., Williams, G.: Trans. Faraday Soc. 56, 1619 (1960)Google Scholar
  77. 77.
    Gustavii, K., Schill, G.: Acta Pharm. Suec. 3, 259 (1966)Google Scholar
  78. 78.
    Guibe, F., Bram, G.: Bull. Soc. Chim. Fr. 1975, 933Google Scholar
  79. 79.
    Illuminati, G.: Solvent effects on selected organic and organometallic reactions. Guidelines to synthetic applications. In: Chemistry 8/2, Dack M. R. J. (ed.), pp. 159–233. New York: Wiley 1976Google Scholar
  80. 80.
    Brändström, A., Kalind-Andersen, H.: Acta Chem. Scand. Ser. B 29, 201 (1975)Google Scholar
  81. 81.
    Brändström, A.: Acta Chem. Scand., Ser. B 30, 203 (1976)Google Scholar
  82. 82.
    Zanger, M., Van der Werf, C. A., McEwen, W. E.: J. Am. Chem. Soc. 81, 3806 (1959)Google Scholar
  83. 83.
    McEwen, W. E. et al.: J. Am. Chem. Soc. 86, 2378 (1964)Google Scholar
  84. 84.
    McEwen, W. E. et al.: J. Am. Chem. Soc. 87, 3948 (1965)Google Scholar
  85. 85.
    Pagilagan, R. U., McEwen, W. E.: Chem. Commun. 1966, 652Google Scholar
  86. 86.
    Campbell, J. B.: U.S. Patent, 3, 639, 492 (1972); Chem. Abstr. 77, 21156 (1972)Google Scholar
  87. 87.
    Pocker, Y., Parker, A. J.: J. Org. Chem. 31, 1526 (1966)Google Scholar
  88. 88.
    Islam, Md. N., Leffek, K. T.: J. Chem. Soc., Perkin Trans. 2 1977, 958Google Scholar
  89. 89.
    Landini, D., Maia, A., Montanari, F.: Nouv. J. Chim. 4, 723 (1980)Google Scholar
  90. 90.
    Yano, Y., Okonogi, T., Tagaki, W.: J. Org. Chem. 38, 3912 (1973)Google Scholar
  91. 91.
    Umezawa, T., Okonogi, T., Tagaki, W.: J. Chem. Soc., Chem. Commun. 1974, 363Google Scholar
  92. 92.
    Yano, Y., Okonogi, T., Tagaki, W.: Bull. Chem. Soc. Japan 47, 771 (1974)Google Scholar
  93. 93.
    Colonna, S., Fornasier, R.: Synthesis 1975, 531Google Scholar
  94. 94.
    Balcells, J., Colonna, S., Fornasier, R.: Synthesis 1976, 266Google Scholar
  95. 95.
    Ref. [37], p. 28Google Scholar
  96. 96.
    Makosza, M., Bialecka, E.: Tetrahedron Lett. 1977, 183Google Scholar
  97. 97.
    Dehmlow, E. V., Lissel, M.: Tetrahedron Lett. 1976, 1783Google Scholar
  98. 98.
    Dehmow, E. V., Lissel, M., Heider, J.: Tetrahedron 33, 363 (1977)Google Scholar
  99. 99.
    Brändström, A., Junggren, U., Lamm, B.: Tetrahedron Lett. 1972, 3173Google Scholar
  100. 100.
    Dehmlow, E. V.: Tetrahedron Lett. 1976, 91Google Scholar
  101. 101.
    Dehmlow, E. V., Remmler, T.: J. Chem. Res. 1977, (S) 72, (M) 766Google Scholar
  102. 102.
    Landini, D., Rolla, F.: Synthesis 1976, 389Google Scholar
  103. 103.
    Fedorynsky, M. et al.: J. Org. Chem. 43, 4682 (1978)Google Scholar
  104. 104.
    Liotta, C. L., Harris, H. P.: J. Am. Chem. Soc. 96, 2250 (1974)Google Scholar
  105. 105.
    Cook, F. L., Bowers, C. W., Liotta, C. L.: J. Org. Chem. 39, 3416 (1974)Google Scholar
  106. 106.
    Tundo, P.: J. Org. Chem. 44, 2048 (1979)Google Scholar
  107. 107.
    Tundo, P., Venturello, P.: Synthesis 1979, 952Google Scholar
  108. 108.
    Angeletti, E., Tundo, P., Venturello, P.: J. Chem. Soc., Chem. Commun. 1980, 1127Google Scholar
  109. 109.
    Angeletti, E., Tundo, P., Venturello, P.: private communicationGoogle Scholar
  110. 110.
    Landini, D. et al.: J. Chem. Soc., Perkin Trans. 2 1980, 46Google Scholar
  111. 111.
    Stott, P. E., Bradshaw, J. S., Parish, W. W.: J. Am. Chem. Soc. 102, 4810 (1980)Google Scholar
  112. 112.
    Landini, D., Montanari, F., Pirisi, F. M.: J. Chem. Soc., Chem. Commun. 1974, 879Google Scholar
  113. 113.
    Landini, D. et al.: Gazz. Chim. Ital. 105, 863 (1975)Google Scholar
  114. 114.
    Makosza, M., Ludwikow, M.: Angew. Chem., Int. Ed. Engl. 13, 665 (1974)Google Scholar
  115. 115.
    Cinquini, M., Tundo, P.: Synthesis 1976, 516Google Scholar
  116. 116.
    Montanari, F., Tundo, P.: Tetrahedron Lett. 1979, 5055Google Scholar
  117. 117.
    Wong, K. H.: J. Chem. Soc., Chem. Commun. 1978, 282Google Scholar
  118. 118.
    Mizuno, T. et al.: Bull. Chem. Soc. Japan 53, 481 (1980)Google Scholar
  119. 119.
    Mathias, L. J., Burkett, D.: Tetrahedron Lett. 1979, 4709Google Scholar
  120. 120.
    Yamashita, J., Ishikawa, S., Hashimoto, H.: Bull. Chem. Soc. Japan 53, 736 (1980)Google Scholar
  121. 121.
    Ref. [37] p. 20Google Scholar
  122. 122.
    Vander Zwan, M. C., Hartner, F. W.: J. Org. Chem. 43, 2655 (1978)Google Scholar
  123. 123.
    Dietrich, B., Lehn, J.-M.: Tetrahedron Lett. 1973, 1225Google Scholar
  124. 124.
    Cinquini, M., Montanari, F., Tundo, P.: J. Chem. Soc., Chem. Commun. 1975, 393Google Scholar
  125. 125.
    Akabori, S., Ohtomi, M.: Bull. Chem. Soc. Japan 48, 2991 (1975)Google Scholar
  126. 126.
    Jeanne, F., Trichet, A.: Compte Rendue de Fin d'Etude, Action Concertée: Activation Selective en Chimie Organique (Catalyse Homogène) 1975Google Scholar
  127. 127.
    Clement, D., Damm, F., Lehn, J.-M.: Heterocycles 5, 477 (1976)Google Scholar
  128. 128.
    Cinquini, M., Montanari, F., Tundo, P.: Gazz. Chim. Ital. 107, 11 (1977)Google Scholar
  129. 129.
    Akabori, S., Tuji, H.: Bull. Chem. Soc. Japan 51, 1197 (1978)Google Scholar
  130. 130.
    Landini, D., Montanari, F., Rolla, F.: Synthesis 1978, 223Google Scholar
  131. 131.
    Buhleier, E., Wehner, W., Vögtle, F.: Chem. Ber. 112, 546 (1979)Google Scholar
  132. 132.
    Landini, D. et al.: J. Am. Chem. Soc. 101, 2526 (1979)Google Scholar
  133. 133.
    Taft, R. W.: Proton transfer equilibria in the gas and solution phases. In: Kinetics of Ion-Molecule Reactions, NATO advanced study, Institute series (B-physics). Ausloss, P. (ed.) 40, 271 (1979)Google Scholar
  134. 134.
    Landini, D. et al.: J. Chem. Soc., Perkin Trans. 2 1981, 821Google Scholar
  135. 135.
    For this nomenclature, see Ref. [136]Google Scholar
  136. 136.
    Vögtle, F., Weber, E.: Angew. Chem., Int. Ed. Engl. 18, 753 (1979)Google Scholar
  137. 137.
    Menger, F. M., Rhee, J. U., Rhee, H. K.: J. Org. Chem. 40, 3803 (1975)Google Scholar
  138. 138.
    Lee, D. G., Chang, V. S.: J. Org. Chem. 43, 1532 (1978)Google Scholar
  139. 139.
    Sanger, W., Suh, I.-H., Weber, G.: Isr. J. Chem. 18, 253 (1979)Google Scholar
  140. 140.
    Vögtle, F., Heimann, U.: Chem. Ber. 111, 2757 (1978)Google Scholar
  141. 141.
    Lehmkuhl, H., Rabet, F., Hauschild, K.: Synthesis 1977, 184Google Scholar
  142. 142.
    Yanagida, S., Noji, Y., Okahara, M.: Tetrahedron Lett. 1977, 2893Google Scholar
  143. 143.
    Aageev, F. Kh. et al.: Azerb. Khim. Zh. 1977, 39; Chem. Abstr. 87, 117 514 (1978)Google Scholar
  144. 144.
    Movsumzade, M. M. et al.: Zh. Org. Khim. 1976, 2477; Chem. Abstr. 86, 71 795 (1977)Google Scholar
  145. 145.
    Hirao, A. et al.: Makromol. Chem. 179, 915 (1978)Google Scholar
  146. 146.
    Hirao, A. et al.: Makromol. Chem. 179, 1735, 2343 (1978)Google Scholar
  147. 147.
    Töke, L., Szabo, G. T., Somogy-Warner, K.: Acta Chim. Sci. Hung. 101, 47 (1979); Chem. Abstr. 92, 65 502 (1980)Google Scholar
  148. 148.
    Balasubramanian, D., Sukumar, P., Chandani, B.: Tetrahedron Lett. 1979, 3543Google Scholar
  149. 149.
    Kitazume, T., Ishikawa, N.: Chem. Lett. 1978, 283Google Scholar
  150. 150.
    Bartsch, R. A., Yang, I. W.: Tetrahedron Lett. 1979, 2503Google Scholar
  151. 151.
    Vögtle, F., Weber, E.: Angew. Chem., Int. Ed. Engl. 13, 814 (1974)Google Scholar
  152. 152.
    Knöchel, A., Oehler, J., Rudolph, G.: Tetrahedron Lett. 1975, 3167Google Scholar
  153. 153.
    Akabori, S., Ohtomi, M., Yatabe, S.: Bull. Chem. Soc. Japan 53, 1463 (1980)Google Scholar
  154. 154.
    Hyatt, J. A.: J. Org. Chem. 43, 1808 (1978)Google Scholar
  155. 155.
    Frensch, K., Vögtle, F.: Liebigs Ann. Chem. 1979, 2121Google Scholar
  156. 156.
    Fornasier, R. et al.: Tetrahedron Lett. 1976, 1381Google Scholar
  157. 157.
    Normant, H., Cuvigny, T., Savignac, P.: Synthesis 1975, 805Google Scholar
  158. 158.
    Tomoi, M. et al.: Chem. Lett. 1976, 473Google Scholar
  159. 159.
    Tomoi, M. et al.: Bull. Chem. Soc. Japan 52, 1653 (1979)Google Scholar
  160. 160.
    Mikolajczyk, M. et al.: Tetrahedron Lett. 1975, 3757Google Scholar
  161. 161.
    Samaan, S., Rolla, F.: Phosphorus Sulfur 4, 145 (1978)Google Scholar
  162. 162.
    Gokel, G. W., Garcia, B. J.: Tetrahedron Lett. 1978, 1743Google Scholar
  163. 163.
    Hayashi, Y.: Japan Kokai 77/111, 486; Chem. Abstr. 88, 104653 (1978)Google Scholar
  164. 164.
    Garcia, B. J., Leopold, A., Gokel, G. W.: Tetrahedron Lett. 1980, 2115Google Scholar
  165. 165.
    Tanaka, T., Mukaiyama, T.: Chem. Lett. 1976, 1259Google Scholar
  166. 166.
    Armstrong, D. W., Kornahrens, H.: Tetrahedron Lett. 1979, 4525Google Scholar
  167. 167.
    Dietrich, B. et al.: Helv. Chim. Acta 62, 2763 (1979)Google Scholar
  168. 168.
    Manecke, G., Storck, W.: Angew. Chem., Int. Ed. Engl. 17, 657 (1978)Google Scholar
  169. 169.
    Regen, S. L.: Angew. Chem., Int. Ed. Engl. 18, 421 (1979)Google Scholar
  170. 170.
    Regen, S. L.: J. Am. Chem. Soc. 97, 5956 (1975)Google Scholar
  171. 171.
    Regen, S. L.: J. Org. Chem. 42, 875 (1977)Google Scholar
  172. 172.
    Zadeh, H. K., Dou, H. J.-M., Metzger, J.: J. Org. Chem. 43, 156 (1978)Google Scholar
  173. 173.
    Cinquini, M. et al.: J. Chem. Soc., Chem. Commun. 1976, 394Google Scholar
  174. 174.
    Molinari, H. et al.: J. Am. Chem. Soc. 101, 3920 (1979)Google Scholar
  175. 175.
    Brown, J. M., Jenkins, J. A.: J. Chem. Soc., Chem. Commun. 1976, 458Google Scholar
  176. 176.
    Molinari, H., Montanari, F., Tundo, P.: J. Chem. Soc., Chem. Commun. 1977, 639Google Scholar
  177. 177.
    Chiles, M. S., Jackson, D. D., Reeves, P. C.: J. Org. Chem. 45, 2915 (1980)Google Scholar
  178. 178.
    Sparrow, J. T.: J. Org. Chem. 41, 1350 (1976)Google Scholar
  179. 179.
    Blasius, E. et al.: Z. Anal. Chem. 284, 337 (1977)Google Scholar
  180. 180.
    Blasius, E., Janzen, K. P., Neumann, W.: Mikrochim. Acta 2, 279 (1977)Google Scholar
  181. 181.
    Blasius, E., Maurer, P. G.: Makromol. Chem. 178, 649 (1977)Google Scholar
  182. 182.
    Takaki, V., Smid, J.: J. Am. Chem. Soc. 96, 2588 (1974)Google Scholar
  183. 183.
    Kopolow, S., Hogen Esch, T. E., Smid, J.: Macromolecules 6, 133 (1973)Google Scholar
  184. 184.
    See Ref. [43], p. 504Google Scholar
  185. 185.
    Montanari, F., Tundo, P.: J. Org. Chem. 46, 2125 (1981)Google Scholar
  186. 186.
    Tomoi, M. et al.: Tetrahedron Lett. 1978, 3031Google Scholar
  187. 187.
    Tomoi, M., Kihara, K., Kakiuchi, H.: Tetrahedron Lett. 1979, 3485Google Scholar
  188. 188.
    Smid, J.: Pure Appl. Chem. 48, 343 (1976)Google Scholar
  189. 189.
    Bogatskii, A. V., Lukyanenko, N. G., Pastushok, V. N.: Dokl. Akad. Nauk SSSR 247, 1153 (1979); Chem. Abstr. 92, 6206 (1980)Google Scholar
  190. 190.
    Regen, S. L., Dulak, L.: J. Am. Chem. Soc. 99, 623 (1977)Google Scholar
  191. 191.
    Regen, S. L., Besse, J. J., McLick, J.: J. Am. Chem. Soc. 101, 116 (1979)Google Scholar
  192. 192.
    Hiratani, K., Reuter, P., Manecke, G.: Isr. J. Chem. 18, 208 (1979)Google Scholar
  193. 193.
    Regen, S. L.: J. Am. Chem. Soc. 99, 3838 (1977)Google Scholar
  194. 194.
    Regen, S. L., Nigam, A., Besse, J. J.: Tetrahedron Lett. 1978, 2757Google Scholar
  195. 195.
    Maeda, H., Hayashi, Y., Teramura, K.: Chem. Lett. 1980, 677Google Scholar
  196. 196.
    McKenzie, W. M., Sherrington, D. C.: J. Chem. Soc., Chem. Commun. 1978, 541Google Scholar
  197. 197.
    Yanagida, S., Takahashi, K., Okahara, M.: J. Org. Chem. 44, 1099 (1979)Google Scholar
  198. 198.
    Montanari, F., Quici, S.: unpublished resultsGoogle Scholar
  199. 199.
    Regen, S. L., Besse, J. J.: J. Am. Chem. Soc. 101, 4059 (1979)Google Scholar
  200. 200.
    Tundo, P.: Synthesis 1978, 315Google Scholar
  201. 201.
    D'Incan, E., Viout, P.: Tetrahedron 31, 159 (1975)Google Scholar
  202. 202.
    Kornblum, N., Seltzer, R., Haberfield, P.: J. Am. Chem. Soc. 85, 1148 (1963)Google Scholar
  203. 203.
    Rolla, F., Roth, W., Horner, L.: Naturwissenschaften 64, 377 (1977)Google Scholar
  204. 204.
    Tundo, P.: J. Chem. Soc., Chem. Commun. 1977, 641Google Scholar
  205. 205.
    Tundo, P., Venturello, P.: J. Am. Chem. Soc. 101, 6606 (1979)Google Scholar
  206. 206.
    Tundo, P., Venturello, P.: J. Am. Chem. Soc. 103, 856 (1981)Google Scholar
  207. 207.
    Dou, H. J.-M. et al.: J. Org. Chem. 42, 4275 (1977)Google Scholar
  208. 208.
    Landini, D., Rolla, F.: Synthesis 1974, 565Google Scholar
  209. 209.
    Landini, D., Rolla, F.: Synthesis 1976, 389Google Scholar
  210. 210.
    Landini, D., Quici, S., Rolla, F.: Synthesis 1975, 430Google Scholar
  211. 211.
    Corey, E. J. et al.: Tetrahedron Lett. 1975, 3183Google Scholar
  212. 212.
    San Filippo, J., Chern, C., Valentino, J. S.: J. Org. Chem. 40, 1678 (1975)Google Scholar
  213. 213.
    Johnson, R. A., Nidy, E. G.: J. Org. Chem. 40, 1680 (1975)Google Scholar
  214. 214.
    See, inter alia Refs. [32]; [35], pp. 73, 85, 96, 109, 117; [36], p. 91, [37], p. 56Google Scholar
  215. 215.
    Makosza, M.: Tetrahedron Lett. 1969, 673Google Scholar
  216. 216.
    Makosza, M. et al.: Tetrahedron 30, 3723 (1974)Google Scholar
  217. 217.
    Gokel, G. W., Korzeniowski, S. H., Blum, L.: Tetrahedron Lett. 1977, 1633Google Scholar
  218. 218.
    Korzeniowski, S. H., Gokel, G. W.: Tetrahedron Lett. 1977, 1637Google Scholar
  219. 219.
    Markezich, R. L. et al.: J. Org. Chem. 42, 3435 (1977)Google Scholar
  220. 220.
    Quan, P. M., Korn, S. R.: Germ. Offenl. 2, 634, 419 (1977); Chem. Abstr. 87, 52942 (1977)Google Scholar
  221. 221.
    Reeves, W. P., Simmons, A., Keller, W.: Synth. Commun. 10, 633 (1980)Google Scholar
  222. 222.
    Montanari, F. et al.: unpublished resultsGoogle Scholar
  223. 223.
    Wilczynski, W., Jawdosiuk, M., Makosza, M.: Rocz. Chem. 51, 1643 (1977)Google Scholar
  224. 224.
    Jawdosiuk, M. et al.: Pol. J. Chem. 52, 2189 (1978)Google Scholar
  225. 225.
    Serio Duggan, A. J., Grabowski, E. J. J., Russ, W. K.: Synthesis 1980, 573Google Scholar
  226. 226.
    Maiorana, S. et al.: unpublished resultsGoogle Scholar
  227. 227.
    Sam, D. J., Simmons, H. E.: J. Am. Chem. Soc. 96, 2252 (1974)Google Scholar
  228. 228.
    Jackman, L. M., Lange, B. C.: Tetrahedron 33, 2737 (1977)Google Scholar
  229. 229.
    Bram, G.: J. Molecular Cat., in pressGoogle Scholar
  230. 230.
    See, inter alia, Refs. [32]; [35], p. 136; [36], p. 170; [37], p. 101Google Scholar
  231. 231.
    See, inter alia, Refs. [32]; [35], p. 125; [36], p. 330; [37], p. 149Google Scholar
  232. 232.
    Landini, D., Quici, S., Rolla, F.: Synthesis 1975, 397Google Scholar
  233. 233.
    Naso, F., Ronzini, L.: J. Chem. Soc., Perkin Trans. 1 1974, 340Google Scholar
  234. 234.
    Chollet, A., Hagenbuch, J. P., Vogel, P.: Helv. Chim. Acta 62, 511 (1979)Google Scholar
  235. 235.
    Makosza, M., Kacprowicz, A., Fedorynski, M.: Tetrahedron Lett. 1975, 2119Google Scholar
  236. 236.
    See, inter alia, Refs. [32]; [35], pp. 18, 58; [36], p. 224; [37],pp. 177, 239Google Scholar
  237. 237.
    See, inter alia, Refs. [32]; [35], pp. 134, 234, 252; [36], pp. 288,341; [37], p. 133Google Scholar
  238. 238.
    Landini, D., Montanari, F., Rolla, F.: Synthesis 1974, 37Google Scholar
  239. 239.
    Landini, D., Montanari, F., Rolla, F.: Synthesis 1978, 771Google Scholar
  240. 240.
    Landini, D., Rolla, F.: J. Org. Chem. 45, 3527 (1980)Google Scholar
  241. 241.
    Rolla, F., Landini, D., Montanari, F.: Inorg. Chim. Acta 40, X138 (1980)Google Scholar
  242. 242.
    Dehmlow, E. V., Slopianka, M.: Chem. Ber. 112, 2765 (1979)Google Scholar
  243. 243.
    Cousseau, J.: Synthesis 1980, 805Google Scholar
  244. 244.
    Sam, D. J., Simmons, H. E.: J. Am. Chem. Soc. 94, 4024 (1972)Google Scholar
  245. 245.
    Weber, W. P., Shepherd, J. P.: Tetrahedron Lett. 1972, 4907Google Scholar
  246. 246.
    Okimoto, T., Swern, D.: J. Am. Oil Chem. Soc. 54, 867 A (1977)Google Scholar
  247. 247.
    Dou, H. J.-M., Komeili-Zadeh, H., Crozet, C.: C. R. Acad. Sci. Paris, Ser. C. 284, 685 (1977)Google Scholar
  248. 248.
    Pletcher, D., Tait, S. J. D.: J. Chem. Soc., Perkin Trans. 2 1979, 788Google Scholar
  249. 249.
    Landini, D., Montanari, F., Rolla, F.: Synthesis 1979, 134Google Scholar
  250. 250.
    Landini, D., Rolla, F.: Chem. Ind. (London) 1980, 213Google Scholar
  251. 251.
    Lee, G. A., Freedman, H. H.: Tetrahedron Lett. 1976, 1641Google Scholar
  252. 252.
    Sy, A. D., Raksis, J. W.: Tetrahedron Lett. 1980, 2223Google Scholar
  253. 253.
    See, inter alia, Refs. [32]; [35], pp. 109, 206; [36], p. 298; [37], p. 249Google Scholar
  254. 254.
    Rylander, P. N.: Organic synthesis with noble metal catalysts, pp. 121–144. New York: Academic Press 1973Google Scholar
  255. 255.
    Lee, D. G., Van den Engh, M.: The oxidation of organic compounds by ruthenium tetroxide. In: Oxidation in Organic Chemistry. Trahanovsky, W. S. (ed.), pp. 177–227. New York: Academic Press 1973Google Scholar
  256. 256.
    Starks, C. M., Napier, D. R.: S. African Patent 7, 101, 495 (1971), Brit. Patent 1, 324, 763 (1973); Chem. Abstr. 76, 153191 (1972)Google Scholar
  257. 257.
    Starks, C. M., Washecheck, P. H.: U.S. Patent 3,547,962 (1970); Chem. Abstr. 74, 140895 (1971)Google Scholar
  258. 258.
    Herriott, A. W., Picker, D.: Tetrahedron Lett. 1974, 1511Google Scholar
  259. 259.
    Napier, D. R., Starks, C. M.: U.S. Patent 3, 992, 432 (1976); Chem. Abstr. 86, 34757 (1977)Google Scholar
  260. 260.
    Ho, T.-L., Gupta, B. G. B., Olah, G. A.: Synthesis 1977, 676Google Scholar
  261. 261.
    Alneri, E., Bottaccio, G., Carletti, V.: Tetrahedron Lett. 1977, 2117Google Scholar
  262. 262.
    Sudnes, L. K.: Acta Chem. Scand., Ser. B. 31, 903 (1977)Google Scholar
  263. 263.
    Pierre, J. L., Handel, H.: Tetrahedron Lett. 1974, 2317Google Scholar
  264. 264.
    Pierre, J. L., Handel, H., Perraud, R.: Tetrahedron 31, 2795 (1975)Google Scholar
  265. 265.
    Handel, H., Pierre, J. L.: Tetrahedron 31, 2799 (1975)Google Scholar
  266. 266.
    Loupy, A., Seyden-Penne, J., Tchoubar, B.: Tetrahedron Lett. 1976, 1677Google Scholar
  267. 267.
    Brändström, A., Jumgren, H., Lamm, B.: Tetrahedron Lett. 1972, 3173Google Scholar
  268. 268.
    Rolla, F.: unpublished resultsGoogle Scholar
  269. 269.
    Borgogno, G., Colonna, S., Fornasier, R.: Synthesis 1975, 529Google Scholar
  270. 270.
    Des Abbayes, H., Alper, H.: J. Am. Chem. Soc. 99, 98 (1977)Google Scholar
  271. 271.
    Reger, D. L., Habib, M. M., Fauth, D. J.: Tetrahedron Lett. 1979, 115Google Scholar
  272. 272.
    Cassar, L.: Ann. N.Y. Acad. Sci. 333, 208 (1980)Google Scholar
  273. 273.
    Cassar, L., Foà, M., Giordano, A.: J. Organomet. Chem. 121, C 55 (1976)Google Scholar
  274. 274.
    Cassar, L., Foà, M.: J. Organomet. Chem. 134, C 15 (1977)Google Scholar
  275. 275.
    Alper, H., Des Abbayes, H.: J. Organomet. Chem. 134, C 11 (1977)Google Scholar
  276. 276.
    Des Abbayes, H., Buloup, A.: J. Chem. Soc., Chem. Commun. 1978, 1090Google Scholar
  277. 277.
    Foà, M., Cassar, L.: Gazz. Chim. Ital. 109, 619 (1979)Google Scholar
  278. 278.
    Cassar, L. et al.: J. Organomet. Chem. 173, C 335 (1979)Google Scholar
  279. 279.
    Yamamura, K., Murakashi, S. I.: Tetrahedron Lett. 1977, 4429Google Scholar
  280. 280.
    Salisova, M., Alper, H.: Angew. Chem., Int. Ed. Engl. 18, 792 (1979)Google Scholar
  281. 281.
    Fiaud, J.-C.: Tetrahedron Lett. 1975, 3495Google Scholar
  282. 282.
    Colonna, S., Fornasier, R.: J. Chem. Soc., Perkin Trans. 1 1978, 371Google Scholar
  283. 283.
    Colonna, S., Hiemstra, H., Wynberg, H.: J. Chem. Soc., Chem. Commun. 1978, 238Google Scholar
  284. 284.
    Colonna, S., Re, A., Wynberg, H.: J. Chem. Soc., Perkin Trans. 1 1981, 547Google Scholar
  285. 285.
    Massé, J. P., Parayre, E. R.: J. Chem. Soc., Chem. Commun. 1976, 438Google Scholar
  286. 286.
    Hiyama, T. et al.: J. Am. Chem. Soc. 98, 1641 (1976)Google Scholar
  287. 287.
    Hiyama, T. et al.: J. Am. Chem. Soc. 97, 1626 (1975)Google Scholar
  288. 288.
    Helder, R. et al.: Tetrahedron Lett. 1976, 1831Google Scholar
  289. 289.
    Wynberg, H., Greijdanus, B.: J. Chem. Soc., Chem. Commun. 1978, 427Google Scholar
  290. 290.
    Ref. [37], p. 256Google Scholar
  291. 291.
    Colonna, S., Fornasier, R., Pfeiffer, U.: J. Chem. Soc., Perkin Trans. 1 1978, 8Google Scholar
  292. 292.
    Hummelen, J. C., Wynberg, H.: Tetrahedron Lett. 1978, 1089Google Scholar
  293. 293.
    Annunizata, R.: Synth. Commun. 9, 171 (1979)Google Scholar
  294. 294.
    Chiellini, E., Solaro, R.: J. Chem. Soc., Chem. Commun. 1977, 231Google Scholar
  295. 295.
    Colonna, S.: private communicationGoogle Scholar

Copyright information

© Springer-Verlag 1982

Authors and Affiliations

  • Fernando Montanari
    • 1
  • Dario Landini
    • 1
  • Franco Rolla
    • 1
  1. 1.Centro C.N.R. and Istituto di Chimica Industriale, UniversitaMilanoItaly

Personalised recommendations