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Maleic Anhydride pp 215–238Cite as

Unusual Reactions

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Abstract

The purpose of this chapter is to introduce a number of useful synthetic reactions. Admittedly, all of these reactions are not unusual in the sense of organic chemistry and a few would have been predicted. However, some are unusual in the sense that they involve both the functional groups of MA. In some cases the ring system is unique for the reaction, for example, in the oxauracil synthesis. Also included in this chapter are 1,3-dipolar cycloadditions. Here too, some cases are given where more than one molecule of MA participates to arrive at quite unusual products. Some of these reactions are very high yielding and they are too useful synthetically to be regarded as extraneous. We believe Sec. 7.2 will justify these comments.

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References

  1. J. Van Alphen, Rec. Trav. Chim. 61, 895 (1942).

    Article  Google Scholar 

  2. M. F. Mayahi and M. F. El-Bermani, Can. J. Chem. 51, 3539 (1973).

    Article  CAS  Google Scholar 

  3. O. Lutz and A. Krauklis, Ber. 69B, 419 (1936).

    CAS  Google Scholar 

  4. E. Rucinschi, I. Gabe, A. Caraculacu, and I. Zugravescu, Rev. Roum. Chim. 13, 637 (1968).

    CAS  Google Scholar 

  5. B. S. Thyagarajan and K. Rajagoplan, Tetrahedron, 19(10), 1483 (1963).

    Article  CAS  Google Scholar 

  6. R. C. Cookson and N. S. Isaacs, Tetrahedron, 19, 1237 (1963).

    Article  CAS  Google Scholar 

  7. G. Caronna, Gazz. Chim. Ital. 78, 38 (1948).

    CAS  Google Scholar 

  8. M. L. Tamayo and J. F. Vanes, An. R. Soc. Esp. Fis. Quim. 43, 777 (1947).

    CAS  Google Scholar 

  9. M. L. Tamayo and F. Alvarez, An. R. Soc. Esp. Fis. Quim. B 48, 75 (1952).

    Google Scholar 

  10. F. Bergmann, J. Am. Chem. Soc. 60, 2811 (1938).

    Article  CAS  Google Scholar 

  11. A. Guingant and J. Renault, C R. Acad Sci. C 279(4), 179 (1974).

    CAS  Google Scholar 

  12. H. R. Snyder, R. B. Hasbrouck, and J. F. Richardson, J. Am. Chem. Soc. 61, 3558 (1939).

    Article  CAS  Google Scholar 

  13. H. R. Snyder, R. H. Levin, and P. F. Wiley, J. Am. Chem. Soc. 60, 2025 (1938).

    Article  CAS  Google Scholar 

  14. G. Caronna, Gazz. Chim. Ital. 11, 482 (1947).

    Google Scholar 

  15. T. Wagner-Jauregg, Ber. 63, 3224 (1930).

    Google Scholar 

  16. T. Wagner-Jauregg, Ber. 63, 3219 (1930).

    Google Scholar 

  17. J. Van Alphen, Rec. Trav. Chim. 61, 892 (1942).

    Article  Google Scholar 

  18. J. R. Bailey and N. H. Moore, J. Am. Chem. Soc. 39, 279 (1917).

    Article  CAS  Google Scholar 

  19. J. Kovacs, V. Bruckner, and I. Kandel, Acta. Chim. Hung. 1, 230 (1951).

    CAS  Google Scholar 

  20. D. B. Dutt and P. C. Guha, J. Indian Chem. Soc. 27(4), 151 (1950).

    CAS  Google Scholar 

  21. W. Hampel, Z Chem. 10, 225 (1970).

    Article  CAS  Google Scholar 

  22. R. Griming and J. Lorberth, J. Organomet. Chem. 69, 213 (1974).

    Article  Google Scholar 

  23. L. L. Rodina, G. B. Martynova, and I. K. Korobitsyna, Zh. Org. Khim. 10(7), 1502 (1974).

    CAS  Google Scholar 

  24. P. DeMaria, F. Gasparini, L. Caglioto, and M. Ghedini, J. Chem. Soc. Perkin Trans., 1922 (1973).

    Google Scholar 

  25. H. Meerwein, E. Buchner, and K. Van Emster, J. Prakt. Chem. 152, 237 (1939).

    Article  CAS  Google Scholar 

  26. L. H. Flett and W. H. Gardner, Maleic Anhydride Derivatives, Wiley, New York (1952).

    Google Scholar 

  27. R. Huisgen, H. Stangl, J. H. Sturm, and H. Wagenhofer, Angew. Chem. 73(5), 170 (1961).

    Article  CAS  Google Scholar 

  28. T. Curtius and K. Raschig, J. Prakt. Chem. 125, 466 (1930).

    Article  CAS  Google Scholar 

  29. T. Curtius and W. Dorr, J. Prakt. Chem. 125, 425 (1930).

    Article  CAS  Google Scholar 

  30. R. Huisgen, G. Szeimies, and L. Moebius, Chem. Ber. 100, 2494 (1967).

    Article  CAS  Google Scholar 

  31. R. Huisgen, H. Hauck, R. Grashey, and H. Seidl, Chem. Ber. 102, 736 (1969).

    Article  CAS  Google Scholar 

  32. M. Joucla and J. Hamlein, C R. Acad. Sci. C, 769 (1971).

    Google Scholar 

  33. R. Huisgen, H. Seidel, and I. Bruning, Chem. Ber. 102, 1102 (1969).

    Article  CAS  Google Scholar 

  34. A. Quilico, G. S. D’Aleontres, and P. Grunanger, Gazz. Chim. Ital. 80, 479 (1950).

    CAS  Google Scholar 

  35. R. Huisgen, Angew Chem. (Int. Ed. Engl.) 2, 565 (1963).

    Article  Google Scholar 

  36. J. R. Gunwell and S. L. Dye, Tetrahedron Lett. 1739 (1975).

    Google Scholar 

  37. R. K. Howe and J. E. Franz, J. Org. Chem. 43, 3742 (1978).

    Article  CAS  Google Scholar 

  38. S. S. Washburne, W. R. Peterson, and D. A. Berman, J. Org. Chem. 37, 1738 (1972).

    Article  CAS  Google Scholar 

  39. J. H. MacMillan, Org. Prep. Proc. Int. 9, 87 (1977).

    Article  CAS  Google Scholar 

  40. J. D. Warren, J. H. McMillan, and S. S. Washburne, J. Org. Chem. 40, 743 (1975).

    Article  CAS  Google Scholar 

  41. H. W. Heine and R. Perry, Tetrahedron Lett. 35, 3123 (1965).

    Article  Google Scholar 

  42. O. W. Webster and R. E. Berson, J. Am. Chem. Soc. 85, 2032 (1963).

    Article  Google Scholar 

  43. G. LaParolla, Gazz. Chim. Ital. 67, 481 (1937).

    Google Scholar 

  44. G. LaParolla, Gazz. Chim. Ital. 73, 94 (1943).

    Google Scholar 

  45. T. Sasaki, K. Kanematsu, and A. Kakechi, Tetrahedron 28, 1469 (1972).

    Article  CAS  Google Scholar 

  46. A. Michael and N. Weiner, J. Am. Chem. Soc. 59, 744 (1937).

    Article  CAS  Google Scholar 

  47. A. Schonberg and A. F. A. Ismail, Nature 144, 910 (1939).

    Article  CAS  Google Scholar 

  48. A. Schonberg and A. F. A. Ismail, J. Chem. Soc., 1375 (1940).

    Google Scholar 

  49. F. Ramirez, N. Ramanathan, and N. B. Desai, J. Am. Chem. Soc. 84, 1317 (1962).

    Article  CAS  Google Scholar 

  50. L. Horner and K. Klupfel, Justus Liebigs Ann. Chem. 591, 69 (1955).

    Article  CAS  Google Scholar 

  51. G. Aksnes, Acta. Chem. Scand. 15, 692 (1961).

    Article  CAS  Google Scholar 

  52. P. A. Choppard and R. F. Hudson, Z Naturforsch. B 18, 509 (1963).

    Google Scholar 

  53. R. F. Hudson and P. A. Choppard, Helv. Chim. Acta. 46, 2178 (1963).

    Article  CAS  Google Scholar 

  54. C. Osuch, J. E. Franz, and F. B. Zienty, J. Org. Chem. 29, 3721 (1964).

    Article  CAS  Google Scholar 

  55. G. Kamai and V. J. Kukhtin, Proc. Acad. Sci. USSR 102, 283 (1955).

    CAS  Google Scholar 

  56. G. M. Kamai and V. A. Kukhtin, Dokl. Akad. Nauk SSSR 109, 91 (1956).

    CAS  Google Scholar 

  57. G. M. Kamai, V. A. Kukhtin, and T. Kazan, Khim. Teknol. Inst. S. M. Kirova 23, 133 (1957).

    CAS  Google Scholar 

  58. R. F. Hudson, Structure and Mechanism in Organo-Phosphorus Chemistry, Academic Press, London (1965).

    Google Scholar 

  59. J. E. McCurry and S. F. Donovan, Tetrahedron Lett. 33, 2869 (1977).

    Article  Google Scholar 

  60. V. W. Armstrong, S. Coulton, R. Ramage, Tetrahedron Lett. 32, 4311 (1976).

    Article  Google Scholar 

  61. P. D. Bartlett, E. F. Cox, and R. E. Davis, J. Am. Chem. Soc. 83, 103 (1961).

    Article  CAS  Google Scholar 

  62. D. S. Tarbel, J. Am. Chem. Soc. 60, 2647 (1938).

    Article  Google Scholar 

  63. C. Weizmann and F. Bergmann, J. Am. Chem. Soc. 60, 2647 (1938).

    Article  CAS  Google Scholar 

  64. R. W. Leeper, Iowa State College J. Sci. 18, 57 (1943).

    CAS  Google Scholar 

  65. V. K. Anderson and J. Munch-Petersen, Acta. Chem. Scand. 16, 947 (1962).

    Article  Google Scholar 

  66. E. Bjerl Nielsen, J. Munch-Petersen, P. Moller Jorgensen, and S. Refn, Acta Chem. Scand. 13, 1943 (1959).

    Article  CAS  Google Scholar 

  67. Organic Reactions, Vol. 19, R. Rittman et al, eds. Academic Press, New York (1972).

    Google Scholar 

  68. J. Munch-Petersen, Bull. Soc. Chim. Fr., 471 (1966).

    Google Scholar 

  69. T. Purdie and P. S. Arup, J. Chem. Soc. 97, 1537 (1910).

    Article  CAS  Google Scholar 

  70. K. Scholtis, Ann. 557, 82 (1945).

    CAS  Google Scholar 

  71. C. S. Marvel, R. L. Meyers, and J. H. Saunders, J. Am. Chem. Soc. 70, 1695 (1948).

    Google Scholar 

  72. N. A. Cortese, C. B. Ziegler, B.J. Hrnjez, and R. F. Heck, J. Org. Chem. 43, 2952 (1978).

    Article  CAS  Google Scholar 

  73. R. McCrindle, K. H. Overton, and R. A. Raphael, J. Chem. Soc. 4798 (1962).

    Google Scholar 

  74. Chemical Economics Handbook, 672.5032u, SRI International, Menlo Park, California (1976).

    Google Scholar 

  75. S. Miroda and M. Miyajima, Hydrocarbon Proc. 49(11), 176 (1970).

    Google Scholar 

  76. D. Braun, A. A. Seyed, and J. Pomakis, Makromol. Chem. 124, 249 (1969).

    Article  CAS  Google Scholar 

  77. I. Schopov, Makromol. Chem. 137, 293 (1970).

    Article  Google Scholar 

  78. H. Zwiefel, J. Loliger, and T. Volker, Makromol. Chem. 153, 125 (1972).

    Article  Google Scholar 

  79. H. Zweifel and T. Volker, Angew Chem. (Internal Ed. Engl.) 11, 342 (1974).

    Google Scholar 

  80. H. Zweifel and T. Volker, Makromol. Chem. 170, 141 (1973).

    Article  CAS  Google Scholar 

  81. E. Berner, J. Chem. Soc., 1052 (1946).

    Google Scholar 

  82. C. W. Bird and P. Molton, Tetrahedron Lett. 17, 1891 (1966).

    Article  Google Scholar 

  83. C. W. Bird and P. Molton, Tetrahedron 23, 4117 (1967).

    Article  CAS  Google Scholar 

  84. R. A. Bailey and G. M. Stunz, Can. J. Chem. 44, 2584 (1966).

    Article  CAS  Google Scholar 

  85. E. Berner and P. Kolsaker, Tetrahedron 24, 1199 (1968).

    Article  CAS  Google Scholar 

  86. G. R. Krow, Ph. D. dissertation, Princeton University, New Jersey (1967).

    Google Scholar 

  87. B. Miya, F. Hoshino, and T. Ono, Div. Petroleum Chem., ACS Dallas, 1973, 18(1), 187 (1973).

    CAS  Google Scholar 

  88. R. Nehring and W. Seelinger, Angew. Chem. (Internat. Ed. Engl.) 9, 460 (1970).

    Article  CAS  Google Scholar 

  89. G. A. Lee, J. Org. Chem. 41, 2656 (1976).

    Article  CAS  Google Scholar 

  90. R. A. Grimm (Ashland Chemical), private communication (Nov. 1979).

    Google Scholar 

  91. M. A. Bulatov, S. G. Mishina, M. A. Mikhailova, and S. S. Spasski, Tr. Inst. Chim. Akad. Nauk SSSR Ural. Filial 13, 69 (1966);

    Google Scholar 

  92. M. A. Bulatov, S. G. Mishina, M. A. Mikhailova, and S. S. Spasski, Chem. Abstr. 67, 87360x (1967).

    Google Scholar 

  93. O. Diels, K. Alder, W. Lubbert, E. Naujoks, F. Ouebernitz, K. Rohl, and H. Segeberg, Ann. 410, 62 (1929).

    Google Scholar 

  94. O. Diels, K. Alder, and D. Winter, Ann. 486, 211 (1931).

    Google Scholar 

  95. O. Diels, K. Alder, H. Winckler, and E. Peterson, Liebigs Ann. Chem. 498, 1–15 (1932).

    Article  Google Scholar 

  96. I. Ogura, K. Soto, M. Yamagushi, and Y. Ohtani, Yagaku Zasshi 91, 1377 (1971).

    CAS  Google Scholar 

  97. S. Ito, H. Takeshita, and T. Makino, Bull. Chem. Soc. Jap. 44, 1982 (1971).

    Article  CAS  Google Scholar 

  98. M. E. Baumann and H. Bosshard, Helv. Chim. Acta 61, 2751 (1978).

    Article  CAS  Google Scholar 

  99. M. E. Baumann and H. Bosshard, Advances in Pesticide Science, Part 2, p. 85, H. Geissbuhler, ed., Pergamon Press, Oxford (1979).

    Google Scholar 

  100. E. Lange and M. Zur Hausen (to Chemische Werke Huels A.G.), Ger. Offen. 2,845,905 (1980).

    Google Scholar 

  101. R. A. Massy-Westropp and M. F. Price, Aust. J. Chem. 33, 333 (1980).

    Article  CAS  Google Scholar 

  102. Y. D. Samuilov, S. E. Soloveva, and A. L. Konovalov, Zh. Org. Khim. 16, 1228 (1980);

    CAS  Google Scholar 

  103. Y. D. Samuilov, S. E. Soloveva, and A. L. Konovalov, Chem. Abstr. 93, 185323 u (1980).

    Google Scholar 

  104. A. Nose and T. Kudo, Yakugaku Zasshi 95, 1390 (1975).

    CAS  Google Scholar 

  105. M. M. Sidky, M. R. Mahran, and L. S. Boulos, Phosphorus Sulfur 8, 365 (1980).

    CAS  Google Scholar 

  106. M. Daneshtalab and K. Motamedi, J. Heterocycl. Chem. 17(4), 785 (1980).

    Article  CAS  Google Scholar 

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  1. Ashland Chemical Company, Dublin, Ohio, USA

    B. C. Trivedi & B. M. Culbertson

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Trivedi, B.C., Culbertson, B.M. (1982). Unusual Reactions. In: Maleic Anhydride. Springer, Boston, MA. https://doi.org/10.1007/978-1-4757-0940-7_7

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  • DOI: https://doi.org/10.1007/978-1-4757-0940-7_7

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