Advertisement

Industrial applications of the wittig reaction

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

Keywords

Retinoic Acid Phosphonium Salt Carotenoid Synthesis Wittig Reaction Triphenylphosphine Oxide 
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.

5 References

  1. 1. a)
    Stepp, W.: Biochem. Z. 22, 452 (1909)Google Scholar
  2. 1. b)
    McCollum, E. V., Davis, M.: J. Biol. Chem. 15, 167; 19, 245 (1914); 23, 181 (1915)Google Scholar
  3. 1. c)
    Karrer, P., Morf, R., Schöpp, K.: Helv. Chim. Acta 14, 1036, 1431 (1931)CrossRefGoogle Scholar
  4. 2. a)
    Schering AG (Inventors H. H. Inhoffen, D. A. van Drop, J. F. Arens), Germ. Pat. Appl., 729, 439 (1944)Google Scholar
  5. 2. b)
    Van Dorp, D. A., Arens, J. F.: Rec. Trav. Chim. Pays-Bas 65, 338 (1946)Google Scholar
  6. 3. a)
    Isler, O. et al.: Helv. Chim. Acta 30, 1911 (1947)CrossRefGoogle Scholar
  7. 3. b)
    Van Dorp, D. A., Arens, J. F.: Nature 160, 189 (1947)Google Scholar
  8. 3. c)
    Arens, J. F., van Dorp, D. A.: Nature 157, 190 (1946)Google Scholar
  9. 4. a)
    Isler, O. et al.: Helv. Chim. Acta 32, 489 (1949)CrossRefGoogle Scholar
  10. 4. b)
    Lindlar, H.: Helv. Chim. Acta 35, 446 (1952)CrossRefGoogle Scholar
  11. 5. a)
    Inhoffen, H. H., Pommer, H., Meth, E. G.: Chemiker Z. 74, 211 (1950)Google Scholar
  12. 5. b)
    Inhoffen, H. H., Pommer, H., Meth, E. G.: Liebigs Ann. Chem. 569, 74 (1950)Google Scholar
  13. 6. a)
    Inhoffen, H. H., Pommer, H., Bohlmann, F.: Chemiker Z. 74, 309 (1950); Liebigs Ann. Chem. 569, 237 (1950); Inhoffen, H. H. et al.: Liebigs Ann. Chem. 570, 54 (1950), Chemiker Z. 74, 285 (1950)Google Scholar
  14. 6. b)
    Karrer, P., Eugster, C. H.: Helv. Chim. Acta 33, 1172 (1950)CrossRefGoogle Scholar
  15. 6. c)
    see also: Milas, N. A. et al.: J. Amer. Chem. Soc. 72, 4844 (1950)CrossRefGoogle Scholar
  16. 7. a)
    Mayer, H., Isler, O., in O. Isler: Carotenoids, Birkhäuser-Verlag, Basel and Stuttgart 1971Google Scholar
  17. 7. b)
    Reppe, K.: Houben Weyl, Vol. V/ld pages 88–137Google Scholar
  18. 8. a)
    Kläui, H., Isler, O.: Chemie in unserer Zeit 15, 1 (1981)CrossRefGoogle Scholar
  19. 8. b)
    Müller, R. K. et al.: Food Chem. 5, 15 (1980)CrossRefGoogle Scholar
  20. 9. a)
    Pommer, H.: Angew. Chem. 72, 811 (1960)Google Scholar
  21. 9. b)
    ibid. 72, 911 (1960)Google Scholar
  22. 9. c)
    ibid. 89, 437 (1977), Angew. Chem. Int. Ed. Engl. 16, 423 (1977)Google Scholar
  23. 10. a)
    Hoffmann, W., Pasedach, H., Pommer, H.: Liebigs Ann. Chem. 729, 52 (1969)Google Scholar
  24. 10. b)
    Carroll, M. F.: J. Chem. Soc. 1941, 507Google Scholar
  25. 11. a)
    Wittig, G., Geissler, G.: Liebigs Ann. Chem. 580, 44 (1953) Reviews on the Wittig reactionGoogle Scholar
  26. 11. b)
    Schöllkopf, U.: Angew. Chem. 71, 260 (1959)Google Scholar
  27. 11. c)
    Maercker, A.: Org. Reactions 14, 270 (1965)Google Scholar
  28. 11. d)
    Johnson, A. W.: Ylide Chemistry, Academic Press, New York, 1966Google Scholar
  29. 11. e)
    Gosney, I., Rowley, A. G., in J. I. G. Cadogan: Organophosphorus Reagents in Organic Synthesis, Academic Press, New York, 1979Google Scholar
  30. 11. f)
    for the mechanism of the Wittig reaction see: Bestmann, H. J.: Pure Appl. Chem. 52, 771 (1980); Giese, B., Schoch, J., Rüchardt, Ch.: Chem. Ber. 111, 1395 (1978)Google Scholar
  31. 12.
    BASF AG (Inventors G. Wittig, H. Pommer) Germ. Pat. 950,552 (1954)Google Scholar
  32. 13. a)
    BASF AG (Inventors W. Reif, B. Schulz, P. Grafen, H.-U. Scholz, H. Grassner), DAS 2,729,974 (1977)Google Scholar
  33. 13. b)
    Hoffmann-La Roche (Inventors K. Schleich, H. Stoller), DAS 2,733,231 (1977)Google Scholar
  34. 14. a)
    Hoffmann-La Roche (Inventors K. Schleich, H. Stoller), DAS 2,636,879 (1976) compare also Märkl, G., Merz, A.: Synthesis 1973, 295 and Boden, R. M.: Synthesis 1975, 784Google Scholar
  35. 15. a)
    Zechmeister, L.: Cis-trans-isomeric Carotenoids, Vitamins A and Arylpolyenes, Springer-Verlag Vienna 1962, page 51Google Scholar
  36. 15. b)
    Reif, W., Grassner, H.: Chem.-Ing.-Tech. 45, 646 (1973)CrossRefGoogle Scholar
  37. 16. a)
    BASF AG (Inventors W. Sarnecki, H. Pommer) Germ. Pat. 1,046046 (1956)Google Scholar
  38. 16. b)
    BASF AG (Inventors W. Sarnecki, H. Pommer) Germ. Pat. 1,060,386 (1957)Google Scholar
  39. 16. c)
    Freyschlag H. et al.: Angew. Chem. 77, 277 (1965), Angew. Chem. Int. Ed. Engl. 4, 287 (1965)Google Scholar
  40. 17. a)
    Michaelis, A., Reese, A.: Chem. Ber. 15, 1610 (1882)Google Scholar
  41. 17. b)
    Maier, L., in: Org. Phosphorus Compounds 1, 1 (1972)Google Scholar
  42. 18.
    BASF AG (Inventors R. Appel, W. Heinzelmann) Germ. Pat. 1,192,205 (1962)Google Scholar
  43. 19. a)
    BASF AG (Inventors G. Wunsch, K. Wintersberger, H. Geierhaas) Germ. Pat. 1,247,310 (1966)Google Scholar
  44. 19. b)
    Wunsch, G., Wintersberger, K., Geierhaas, H.: Z. anorg. allg. Chem. 369, 33 (1969)CrossRefGoogle Scholar
  45. 20.
    Hoffmann-La Roche (Inventors E. A. Broger) Europ. Pat. 5,747 (1978)Google Scholar
  46. 21. a)
    UBE Industries, Ltd. JP 057009 (1979)Google Scholar
  47. 21. b)
    Masaki, M., Kakeya, N.: Angew. Chem. 89, 558 (1977), Angew. Chem. Int. Ed. Engl. 16, 552 (1977)Google Scholar
  48. 22.
    Texas Alkyls Inc. (Inventors D. B. Malpass, G. S. Yeargin), DAS 2,714,721 (1973)Google Scholar
  49. 23.
    Hoffmann-La Roche (Inventors J. N. Gardner, J. Köchling), DAS 2,437,153 (1973)Google Scholar
  50. 24. a)
    M+T Chemicals Inc. (Inventors W. R. Davis, M. D. Gordon), DAS 2,828,604 (1978)Google Scholar
  51. 24. b)
    Hoffmann-La Roche (Inventors J. M. Townsend, D. H. Valentine jun.), DAS 2,455,371 (1973)Google Scholar
  52. 25.
    Wittig, G.: personal communication (1957), see also under 9bGoogle Scholar
  53. 26.
    BASF AG (Inventors W. Stilz, H. Pommer)Google Scholar
  54. 26. a)
    Germ. Pat. 1,092,472 (1958)Google Scholar
  55. 26. b)
    Germ. Pat. 1,109,671 (1958)Google Scholar
  56. 26. c)
    Germ. Pat. 1,108,208 (1959)Google Scholar
  57. 27. a)
    Horner, L., Hoffmann, H., Wippel, H. G.: Chem. Ber. 91, 61 (1958)Google Scholar
  58. 27. b)
    Horner, L. et al.: Chem. Ber. 92, 2499 (1959)Google Scholar
  59. 28. a)
    More recent reviews: Walker, B. J., in J. I. G. Cadogan: Organophosphorus Reagents in Organic Chemistry, Academic Press, New York, 1979Google Scholar
  60. 28. b)
    Wadsworth Jr., W. S.: Organ. React. 25, 73 (1978)Google Scholar
  61. 28. c)
    Boutagy, J., Thomas, R.: Chem. Rev. 74, 87 (1974)CrossRefGoogle Scholar
  62. 29.
    Stilz, W.: Thesis, Univers. Tübingen 1954Google Scholar
  63. 30. a)
    BASF AG (Inventors W. Stilz, H. Pommer) Germ. Pat. 1,108,219 (1959)Google Scholar
  64. 30. b)
    BASF AG (Inventors W. Stilz, H. Pommer, K.-H. König) Germ. Pat. 1,112,072 (1959)Google Scholar
  65. 31.
    Hoffmann-La Roche (Inventors H. Stoller, H. P. Wagner), DAS 2,439,860 (1973)Google Scholar
  66. 32.
    Hoffmann-La Roche (Inventors M. Lalonde, H. Stoller), DAS 2,548,883 (1975)Google Scholar
  67. 33.
    BASF AG (Inventors M. Fischer, W. Wiersdorf, A. Nürrenbach, D. Horn, F. Feichtmayer), DAS 2,210,800 (1972)Google Scholar
  68. 34. a)
    Pommer, H., Nürrenbach, A.: Pure Appl. Chem. 43, 527 (1975)Google Scholar
  69. 34. b)
    Paust, J., Reif, W., Schumacher, H.: Liebigs Ann. Chem. 1976, 2194Google Scholar
  70. 34. c)
    BASF AG (Inventors H. Freyschlag, W. Reif, A. Nürrenbach, H. Pommer), DAS 1,216,962 (1964), 1,211,616 (1963)Google Scholar
  71. 34. c1)
    BASF AG (Inventors H. Freyschlag, W. Reif, A. Nürrenbach, W. Sarnecki) Germ. Pat. 1,210,832 (1963)Google Scholar
  72. 34. d)
    see reference 45 a)Google Scholar
  73. 35. a)
    Isler, O.: Pure Appl. Chem. 51, 447 (1979)Google Scholar
  74. 35. b)
    Kienzle, F.: Pure Appl. Chem. 47, 183 (1976)Google Scholar
  75. 36.
    Meuly, W. C.: Riechstoffe, Aromen, Körperpflegemittel 22, 191 (1972)Google Scholar
  76. 37.
    BASF AG (Inventors H. Pommer, H. Müller, H. Overwien) Germ. Pat. 1,259,876 (1966)Google Scholar
  77. 38.
    Straub, O.: Key to Carotenoids: List of Neutral Carotenoids, Birkhäuser-Verlag, Basel, Stuttgart, 1976Google Scholar
  78. 39.
    Thommen, H.: Pure Appl. Chem. 51, 867 (1979)Google Scholar
  79. 40.
    BASF AG (Inventors H. Pommer, W. Sarnecki) Germ. Pat. 1,068,710 (1958) and 1,068,703 (1958)Google Scholar
  80. 41. a)
    BASF AG (Inventors W. Sarnecki, A. Nürrenbach, W. Reif) Germ. Pat. 1,155,126 (1963) and 1,158,505 (1963)Google Scholar
  81. 41. b)
    Schwieter, U. et al.: Helv. Chim. Acta 49, 369 (1966)CrossRefGoogle Scholar
  82. 42. a)
    BASF AG (Inventors H. Pommer, W. Sarnecki) Germ. Pat. 1,068,709 (1958)Google Scholar
  83. 42. b)
    see ref. 9bGoogle Scholar
  84. 43. a)
    Bestmann, H. J., Kratzer, O.: Chem. Ber. 96, 1899 (1963)Google Scholar
  85. 43. b)
    Bestmann, H. J., Kisielowski, L., Distler, W.: Angew. Chem. 88, 297 (1976), Angew. Chem. Int. Ed. Engl. 15, 298 (1976)Google Scholar
  86. 44. a)
    BASF AG (Inventors B. Schulz, J. Paust, J. Schneider) Germ. Pat. 2,505,869 (1975)Google Scholar
  87. 44. b)
    Nürrenbach, A. et al.: Liebigs Ann. Chem. 1977, 1146Google Scholar
  88. 45. a)
    BASF AG (Inventors H. Freyschlag, W. Reif, A. Nürrenbach, H. Pommer), Germ. Pat. 1,210,780 (1963)Google Scholar
  89. 45. b)
    see ref. 34aGoogle Scholar
  90. 46.
    BASF AG (Inventor H. Jaedicke), DAS 2,851,051 (1978)Google Scholar
  91. 47.
    Mayer, H.: Pure Appl. Chem. 51, 535 (1979)Google Scholar
  92. 48. a)
    Hoffmann-La Roche (Inventor J. D. Surmatis), US Pat. 3,311,656 (1964)Google Scholar
  93. 48. b)
    Hoffmann-La Roche (Inventor M. Rosenberger), DAS 2,801,908 (1977)Google Scholar
  94. 49.
    BASF AG (Inventors H. Jaedicke, J. Paust, J. Schneider) Germ. Pat. 2,534,807 (1975), 2,534,805 (1975)Google Scholar
  95. 50. a)
    Yokoyama, H., White, M. J.: J. Org. Chem. 30, 2481 (1965)Google Scholar
  96. 50. b)
    see ref. 9c and 45aGoogle Scholar
  97. 51. a)
    Entschel, R., Karrer, P.: Helv. Chim. Acta 41, 402,983 (1958)Google Scholar
  98. 51. b)
    see ref. 35aGoogle Scholar
  99. 52. a)
    Stüttgen, G.: Dermatologica 124, 65 (1962)PubMedGoogle Scholar
  100. 52. b)
    König, H. et al.: Arzneimittel-Forsch. 24, 1184 (1974), and subsequent papersGoogle Scholar
  101. 53. a)
    Sporn, M. B., Newton, D. L.: Fed. Proc. 38, 2528 (1979)PubMedGoogle Scholar
  102. 53. b)
    Newton, D. L., Henderson, W. R., Sporn, M. B.: Cancer Res. 40, 3413 (1980)PubMedGoogle Scholar
  103. 54.
    Peto, R. et al.: Nature 290, 201 (1981)Google Scholar
  104. 55. a)
    Ronneberg, H. et al.: Helv. Chim. Acta 63, 711 (1980)CrossRefGoogle Scholar
  105. 56. b)
    Schiedt, K., Leuenberger, F. J., Vecchi, M.: Helv. Chim. Acta 64, 449 (1981), Kuhn, R., Sörensen, N. A.: Ber. deut. chem. Ges. 71, 1879 (1938)CrossRefGoogle Scholar
  106. 57. a)
    Kienzle, F., Mayer, H.: Helv. Chim. Acta 61, 2609 (1978)CrossRefGoogle Scholar
  107. 57. b)
    Hoffmann-La Roche (Inventors E. A. Broger, Y. Crameri, H. G. W. Leuenberger, E. Widmer, R. Zell) Europ. Pat. 5,748 (1978)Google Scholar
  108. 57. c)
    Widmer, E. et al.: Abstr. 6. Int. Symp. Carotenoids, July 1981, LiverpoolGoogle Scholar
  109. 58. a)
  110. 58. b)
    Hoffmann-La Roche (Inventors U. Schwieter, R. Rüegg) Germ. Pat. 1,247,299 (1968)Google Scholar
  111. 58. c)
    Isler, O. et al.: Helv. Chim. Acta 42, 864 (1959)CrossRefGoogle Scholar

Copyright information

© Springer-Verlag 1983

Authors and Affiliations

  1. 1.BASF AktiengesellschaftLudwigshaften/Rh.FRG

Personalised recommendations