Advertisement

The calixarenes

  • C. David Gutsche
Conference paper
Part of the Topics in Current Chemistry book series (TOPCURRCHEM, volume 123)

Keywords

Partial Cone Cyclic Oligomer Linear Oligomer Dibenzyl Ether Clathrate Compound 
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.

11 References

  1. 1.
    Cram, D. J., Cram, J. M.: Science 183, 803 (1974)Google Scholar
  2. 2.
    Lehn, J. M.: Pure Applied Chem. 50, 871 (1978)Google Scholar
  3. 3.
    Gutsche, C. D., Muthukrishnan, R.: J. Org. Chem. 43, 4905 (1978)CrossRefGoogle Scholar
  4. 4.
    Gutsche, C. D.: Accts. Chem. Res. 16, 161 (1983)CrossRefGoogle Scholar
  5. 5.
    Patterson, A. M., Capell, L. T., Walker, D. F.: The Ring Index, 2nd. ed., Amer. Chem. Soc., Washington, D.C., 1960, Ring Index No. 6485Google Scholar
  6. 6.
    Cram, D. J., Steinberg, H.: J. Am. Chem. Soc. 73, 5691 (1951)CrossRefGoogle Scholar
  7. 7.
    IPUAC Tentative Rules for Nomenclature of Organic Chemistry, Section. E. Fundamental Stereochemistry; cf. J. Org. Chem. 35, 2849 (1970)Google Scholar
  8. 8.
    Zinke, A., Kretz, R., Leggewie, E., Hössinger, K.: Monatsh. Chem. 83, 1213 (1952)CrossRefGoogle Scholar
  9. 9.
    Hayes, B. T., Hunter, R. F.: Chem. Ind., 193 (1956): J. Applied Chem. 8, 743 (1958)Google Scholar
  10. 10.
    Cornforth, J. W., D'Arcy Hart, P., Nicholls, G. A., Rees, R. J. W., Stock, J. A.: Brit. J. Pharmacol. 10, 73 (1955)Google Scholar
  11. 11.
    We are indebted to Dr. Kurt L. Loening of Chemical Abstract Services for his guidance in questions concerning the numbering of these compounds, which follows the IUPAC guidelines as noted for compound 2 in Fig. 1Google Scholar
  12. 12.
    Högberg, A. G. S.: PhD Dissertation, Royal Institute of Technology, Stockhom, 1977. We are indebted to Dr. Högberg for making available to us this excellent thesis which suggests the “intraannular” and “extraannular” terminologyGoogle Scholar
  13. 13.
    Beyer, A.: Ber. dtsch. chem. Ges. 5, 25, 280, 1094 (1872)Google Scholar
  14. 14.
    Numerous accounts of the history of phenol-formaldehyde resins are available, including Baekeland, L. H.: Ind. Eng. Chem. (Industry) 5, 506 (1913); Carswell, T. S.: Phenoplasts, Interscience Publishers, Inc., New York, 1947; Gillis, J., Oesper, R. E.: J. Chem. Ed. 41, 224 (1964)CrossRefGoogle Scholar
  15. 15.
    Zinke, A., Ziegler, E.: Ber. dtsch. chem. Ges. 74, 1729 (1941)Google Scholar
  16. 16.
    Zinke, A., Ziegler, E.: ibid. 77B, 264 (1944)Google Scholar
  17. 17.
    Zinke, A., Zigeuner, G., Hössinger, K., Hoffmann, G.; Monatsh. Chem. 79, 438 (1948)CrossRefGoogle Scholar
  18. 18.
    Zinke, A., Ott, R., Garrana, F. H.: Monatsch. Chem. 89, 135 (1958)CrossRefGoogle Scholar
  19. 19.
    Zinke, A.: J. Appl. Chem. 1, 257 (1951)Google Scholar
  20. 20.
    Kämmerer, H., Happel, G., Caesar, F.: Makromol. Chem. 162, 179 (1972)CrossRefGoogle Scholar
  21. 21.
    Happel, G., Mathiasch, B., Kämmerer, H.: Makromol. Chem. 176, 3317 (1975)CrossRefGoogle Scholar
  22. 22.
    Munch, J. H.: Makromol. Chem. 178, 69 (1977)CrossRefGoogle Scholar
  23. 23.
    Gutsche, C. D., Dhawan, B., No, K. H., Muthukrishnan, R.: J. Am. Chem. Soc. 103, 3782 (1981)CrossRefGoogle Scholar
  24. 24.
    Gutsche, C. D., Muthukrishnan, R., No, K. H.: Tetrahedron Lett. 2213 (1979)Google Scholar
  25. 25.
    Muthukrishnan, R., Gutsche, C. D.: J. Org. Chem. 44, 3962 (1979)CrossRefGoogle Scholar
  26. 26.
    Ninagawa, A., Matsuda, H.: Makromol. Chem. Rapid Comm. 3, 65 (1982)CrossRefGoogle Scholar
  27. 27.
    Nakamoto, Y., Ishida, S.:: ibid. 3, 705 (1982)CrossRefGoogle Scholar
  28. 28.
    Mukoyama, Y., Tanno, T.: Org. Coating & Plastics Chem. 40, 894 (1979)Google Scholar
  29. 29.
    Andreetti, G. D., Ungaro, R., Pochini, A.: J. Chem. Soc. Chem. Comm. 1005 (1979)Google Scholar
  30. 30.
    Andreetti, G. D., Pochini, A., Ungaro, R.: J. Chem. Soc., Perkin II, 1773 (1983)Google Scholar
  31. 31.
    Ninagawa, A.: private communicationGoogle Scholar
  32. 32.
    Coruzzi, M., Andreetti, G. D., Bocchi, V., Pochini, A., Ungaro, R.: J. Chem. Soc., Perkin II, 1133 (1982)Google Scholar
  33. 33.
    Andreetti, G. D., Ungaro, R., Pochini, A.: Abstr. 2nd Internat. Symp. on Clathrate Compounds and Molecular Inclusion Phenomena, Parma, 1982, p. 88Google Scholar
  34. 34.
    Andreetti, G. D., Ungaro, R., Pochini, A.: J. Chem. Soc. Chem. Comm. 533 (1981)Google Scholar
  35. 35.
    Raschig, F.: Z. für angew. Chem. 25, 1939 (1912)Google Scholar
  36. 36.
    Baekeland, L. H.: J. Ind. Eng. Chem. (Industry) 5, 506 (1913)CrossRefGoogle Scholar
  37. 37.
    Niederl, J. B., McCoy, J. S.: J. Am. Chem. Soc. 65, 629 (1943)CrossRefGoogle Scholar
  38. 38.
    Koebner, M.: Z. Angew. Chem. 46, 251 (1933)Google Scholar
  39. 39.
    Finn, S. R., Lewis, G. J.: J. Chem. Soc. Ind. 69, 132 (1950)Google Scholar
  40. 40.
    Foster, H. M., Hein, D. W.: J. Org. Chem. 26, 2539 (1961)CrossRefGoogle Scholar
  41. 41.
    The p-tert-butylcalix[8]arene and p-(1,1,3,3-tetramethylbutyl)calix[8]arene have been correlated by removing the alkyl groups from each of these compounds and obtaining the same calix[8]arene (8, R=H)32 Google Scholar
  42. 42.
    Gutsche, C. D., Kung, T. C., Hsu, M.-L.: Abstr. 11th Midwest Regional Meet. Amer. Chem. Soc., Carbondale, IL, 1975, no. 517Google Scholar
  43. 43.
    Patrick, T. B., Egan, P. A.: J. Org. Chem. 42, 382 (1977)CrossRefGoogle Scholar
  44. 44.
    Patrick and Egan 43) reported molecular weights for their products using either mass spectroscopy or the Rast method (camphor as solvent). However, unless the absence of m/e signals higher than that of the anticipated parent ion (i.e. cyclic tetramer) is demonstrated, the mass spectral data can be misleading. The Rast method, requiring the compound to be at least moderately soluble in camphor, would appear to be inapplicable in the case of the cyclic oligomers, all of which are quite insoluble in most organic materialsGoogle Scholar
  45. 45.
    Chen, S. I.; unpublished observationsGoogle Scholar
  46. 46.
    Pagoria, P. F.: unpublished observationsGoogle Scholar
  47. 47.
    Buriks, R. S., Fauke, A. R., Munch, J. H.: U.S. Patent 4,259,464, filed 1976, issued 1981Google Scholar
  48. 48.
    Levine, J. A.: unpublished observationsGoogle Scholar
  49. 49.
    Stewart, D.: unpublished observationsGoogle Scholar
  50. 50.
    Ullman, F., Brittner, K.: Ber. dtsch. chem. Ges. 42, 2539 (1909)Google Scholar
  51. 51.
    Wohl, A., Mylo, B.: ibid. 45, 2046 (1912)Google Scholar
  52. 52.
    Hultzsch, K.: ibid. 75B, 106 (1942)Google Scholar
  53. 53.
    v. Euler, H., Adler, E., Cedwall, J. O., Törngren, O.: Ark. f. Kemi Mineral. Geol. 15A, No. 11, 1 (1941)Google Scholar
  54. 54.
    Gardner, P. D., Sarrafizadeh, H., Brandon, R. L.: J. Am. Chem. Soc. 81, 5515 (1959)CrossRefGoogle Scholar
  55. 55.
    Wegler, R., Herlinger, H.: Methoden der Organischen Chemie (Houben-Weyl), XIV/2; Makromolecular Stoffe, Thieme Verlag, Stuttgart, 1963, p. 257Google Scholar
  56. 56.
    Evans, D. A., Golob, A. M.: J. Am. Chem. Soc. 97, 4765 (1975); Thies, R. W., Seitz, E. P.: J. Org. Chem. 43, 1050 (1978)CrossRefGoogle Scholar
  57. 57.
    Adler, E.: Arkiv. f. Kemi Mineral. Geol. 14B, No. 23, 1 (1941)Google Scholar
  58. 58.
    v. Euler, H., Adler, E., Bergstrom, B.: Arkiv. f. Kemi Geol., 14B, No. 25, 1 (1941); Hultzsch, K.: Kunststoffe 52, 19 (1962)Google Scholar
  59. 59.
    Zinke, A., Ziegler, E., Hontschik, I.: Monatsh. Chem. 78, 317 (1948); Ziegler, E., Hontschik, I.: ibid. 78, 325 (1948)CrossRefGoogle Scholar
  60. 60.
    In addition to water and formaldehyde, other extrusion products, such as benzaldehydes, have also been shown to be formed upon heating mixtures above 150 °C 59)Google Scholar
  61. 61.
    Cairns, T., Eglinton, G.: Nature 196, 535 (1962)Google Scholar
  62. 62.
    Dhawan, B., Gutsche, C. D.: J. Org. Chem. 48, 1536 (1983)CrossRefGoogle Scholar
  63. 63.
    Izatt, R. M., Lamb, J. D., Hawkins, R. T., Brown, P. R., Izatt, S. R., Christensen, J. J.: J. Am. Chem. Soc. 105, 1782 (1983)CrossRefGoogle Scholar
  64. 64.
    Burke, W. J., Craven, W. E., Rosenthal, A., Ruetman, S. H., Stephens, C. W., Weatherbee, C.: J. Polymer Sci. 20, 75 (1956)Google Scholar
  65. 65.
    Dhawan, B.: unpublished observationsGoogle Scholar
  66. 66.
    Michael, A.: Amer. Chem. J. 5, 338 (1883)Google Scholar
  67. 67.
    Niederl, J. B., Vogel, H. J.: J. Am. Chem. Soc. 62, 2512 (1940)CrossRefGoogle Scholar
  68. 68.
    Erdtman, H., Haglid, F., Ryhage, R.: Acta Chem. Scand. 18, 1249 (1964)Google Scholar
  69. 69.
    Erdtman, H., Högberg, S., Abrahamsson, S., Nilsson, B.: Tetrahedron Lett. 1679 (1968); Nilsson, B.: Acta. Chem. Scand. 22, 732 (1968)Google Scholar
  70. 70.
    Palmer, K. J., Wong, R. Y., Jurd, L., Stevens, K.: Acta Crystallogr. B32, 847 (1976)Google Scholar
  71. 71.
    Högberg, A. G. S.: J. Org. Chem. 45, 4498 (1980)CrossRefGoogle Scholar
  72. 72.
    Högberg, A. G. S.: J. Am. Chem. Soc. 102, 6046 (1980)CrossRefGoogle Scholar
  73. 73.
    Additional evidence for the acid-lability of the cyclic tetramers (13) is seen in their tendency to undergo nitrodealkylation. For example, treatment of 13 (R = Phenyl, R′ = Methyl) with concentrated nitric acid yields 4,6-dinitroresorcinol dimethyl ether and 3,5-dinitrobenzoic acid 12)Google Scholar
  74. 74.
    Ballard, J. L., Kay, W. B., Kropa, E. L.: J. Paint Technol. 38, 251 (1966)Google Scholar
  75. 75.
    Bottino, F., Montaudo, G., Maravigna, P.: Ann. Chim. (Rome) 57, 972 (1967)Google Scholar
  76. 76.
    Brown, W. H., Hutchinson, B. J.: Can. J. Chem. 56, 617 (1978) and preceding papers back to Brown, W. H., Sawatsky, H.: ibid. 34, 1147 (1956)Google Scholar
  77. 77.
    Chastrette, M., Chastrette, F.: J. Chem. Soc. Chem. Comm. 534 (1973)Google Scholar
  78. 78.
    Healy, M. de S., Rest, A. J.: J. Chem. Soc. Chem. Comm. 140 (1981)Google Scholar
  79. 79.
    Högberg, A. G. S., Weber, M.: Acta. Chem. Scand. B 37, 55 (1983)Google Scholar
  80. 80.
    Ahmed, M., Meth-Cohn, O.: Tetrahedron Lett. 1493 (1969); J. Chem. Soc. C 2104 (1971)Google Scholar
  81. 81.
    Rothemund, P., Gage, C. L.: J. Am. Chem. Soc. 77, 3340 (1955)CrossRefGoogle Scholar
  82. 82.
    Collman, J. P., Gagne, R., Reed, C., Halbert, T. R., Lang, G., Robinson, W. T.: J. Am. Chem. Soc. 97, 1427 (1975)PubMedGoogle Scholar
  83. 83.
    Robinson, G. M.: J. Chem. Soc. 107, 267 (1915); Collet, A., Gabard, J.: J. Org. Chem. 45, 5400 (1980) and references thereinGoogle Scholar
  84. 84.
    Freeman, W. A., Mock, W. L., Shih, N.-Y.: J. Am. Chem. Soc. 103, 7367 (1981)CrossRefGoogle Scholar
  85. 85.
    Meth-Cohn, O.: Tetrahedron Lett. 91 (1973)Google Scholar
  86. 86.
    Sawa, N., Nomoto, T., Aida, K., Suzuki, T.: J. Synth. Org. Chem. 33, 1007 (1975)Google Scholar
  87. 87.
    Bergman, J., Högberg, S., Lindström, J.-O.: Tetrahedron 26, 3347 (1970); Raverty, W. D., Thomson, R. H., King, T. J.: J. Chem. Soc., Perkin I, 1204 (1977)CrossRefGoogle Scholar
  88. 88.
    Hunter, R. F., Turner, C.: Chem. Ind., 72 (1957) also reported the synthesis of a cyclic octamer containing six m-bridges and two p-bridges, the remaining four m-positions being “blocked” with methyl groupsGoogle Scholar
  89. 89.
    Kämmerer, H., Happel, G.: Makromol. Chem. 179, 1199 (1978)CrossRefGoogle Scholar
  90. 90.
    Kämmerer, H., Happel, G., Böhmer, V., Rathay, D.: Monatsh. Chem. 109, 767 (1978)CrossRefGoogle Scholar
  91. 91.
    Kämmerer, H., Happel, G.: Makromol. Chem. 181, 2049 (1980)CrossRefGoogle Scholar
  92. 92.
    Kämmerer, H., Happel, G.: ibid. 112, 759 (1981)Google Scholar
  93. 93.
    Kämmerer, H., Happel, G., Mathiasch, B.: ibid. 182, 1685 (1981)CrossRefGoogle Scholar
  94. 94.
    Kämmerer, H., Happel, G.: in: Weyerhaeuser Science Symposium on Phenolic Resins, Tacoma, Washington, 1979, p. 143Google Scholar
  95. 95.
    Gutsche, C. D.; No, K. H.: J. Org. Chem. 47, 2708 (1982)CrossRefGoogle Scholar
  96. 96.
    Böhmer, V., Chhim, P., Kämmerer, H.: Makromol. Chem. 180, 2503 (1979)CrossRefGoogle Scholar
  97. 97.
    Moshfegh, A. A., Badri, R., Hojjatie, M., Kaviani, M., Naderi, B., Nazmi, A. H., Ramezanian, M., Roospeikar, B., Hakimelahi, G. H.: Helv. Chim. Acta. 65, 1221 (1982)CrossRefGoogle Scholar
  98. 98.
    Moshfegh, A. A., Mazandarani, B., Nahid, A., Hakimelahi, G. H.: Helv. Chim. Acta 65, 1229 (1982)CrossRefGoogle Scholar
  99. 99.
    Moshfegh, A. A., Baladi, E., Radnia, L., Afsanch, S. L. R., Hosseini, A. S., Tofigh, S., Hakimelahi, G. H.: Helv. Chim. Acta 65, 1264 (1982)CrossRefGoogle Scholar
  100. 100.
    No, K. H., Gutsche, C. D.: J. Org. Chem. 47, 2713 (1982)CrossRefGoogle Scholar
  101. 101.
    Hultzsch, K.: Kunststoffe 52, 19 (1962)Google Scholar
  102. 102.
    von Euler, H., Adler, E., Bergstrom, B.: Ark. Kemi. Mineral Geol. 14B, No. 30, 1 (1941)Google Scholar
  103. 103.
    Kämmerer, H., Dahm, M.: KunstPlast (Solothurn Switz.) 6, 20 (1959)Google Scholar
  104. 104.
    Still, W. C., Kahn, M., Mitra, A.: J. Org. Chem. 43, 2923 (1978)CrossRefGoogle Scholar
  105. 105.
    Kricheldorf, H. R., Kaschig, J.: Liebigs Ann. Chem. 882 (1976)Google Scholar
  106. 106.
    Bocchi, V., Foina, D., Pochini, A., Ungaro, R.: Tetrahedron 38, 373 (1982)CrossRefGoogle Scholar
  107. 107.
    Gutsche, C. D., Dhawan, B., Levine, J. A., No, K. H., Bauer, L. J.: Tetrahedron 39, 409 (1983)CrossRefGoogle Scholar
  108. 108.
    Cornforth, J. W., Morgan, E. D., Potts, K. T., Rees, R. J. W.: Tetrahedron 29, 1659 (1973)CrossRefGoogle Scholar
  109. 109.
    Klebe, J. F., Finkbeiner, H., White, D. M.: J. Am. Chem. Soc. 88, 3390 (1966)CrossRefGoogle Scholar
  110. 110.
    (a) Gutsche, A. E.: unpublished observations; (b) Ludwig, F. J.: unpublished observationsGoogle Scholar
  111. 111.
    We are indebted to Mr. Christopher Cramer for devising a computer program for comparing the “fingerprint” region data for a variety of calixarenesGoogle Scholar
  112. 112.
    Megson, N. R. L.: Oesterr. Chem. Z. 54, 317 (1953)Google Scholar
  113. 113.
    Ott, R., Zinke, A.: Oesterr. Chem. Z. 55, 156 (1954)Google Scholar
  114. 114.
    Gutsche, C. D., Bauer, L. J.: Tetrahedron Lett. 4763 (1981)Google Scholar
  115. 115.
    Saenger, W., Betzel, C., Brown, G. M.: Angew. Chem. Int. Ed. Engl. 22, 883 (1983); Saenger, W., Betzel, C., Hingerty, B., Brown, G. M.: Nature 296, 581 (1982); Saenger, W.: ibid, 279, 343 (1979)CrossRefGoogle Scholar
  116. 116.
    Bauer, L. J.: unpublished observationsGoogle Scholar
  117. 117.
    Helgeson, R. C., Mazaleyrat, J.-P., Cram, D. J.: J. Am. Chem. Soc. 103, 3929 (1981)CrossRefGoogle Scholar
  118. 118.
    Moran, J. R., Karbach, S., Cram, D. J.: J. Am. Chem. Soc. 104, 5826 (1982); Cram, D. J.: Science 219, 1177 (1983)CrossRefGoogle Scholar
  119. 119.
    Rizzoli, C., Andreetti, G. D., Ungaro, R., Pochini, A.: J. Molec. Structure 82, 133 (1982)CrossRefGoogle Scholar
  120. 120.
    The formation of two “partial cone” compounds is the result of the reduced symmetry of 41 (R = tert-Bu) which gives rise to six conformers; viz. one “cone”, two “partial cone”, two “1,2-alternate”, and one “1,3-alternate”Google Scholar
  121. 121.
    Dradi, E., Pochini, A., Ungaro, R.: Abstr. 2nd Internat. Symposium on Clathrate Compounds and Molecular Inclusion Phenomena, Parma/Italy, 1982, p. 84Google Scholar
  122. 122.
    Bailey, D. W.: unpublished observationsGoogle Scholar
  123. 123.
    See Tashiro, M.: Synthesis, 921 (1979) for general references and see Böhmer, V., Rathay, D., Kämmerer, H.: Org. Prep. Proc. Int. 10, 113 (1978) for a closely analogous exampleGoogle Scholar
  124. 124.
    Compound 61, which melts at 248–250 °C, can be demethylated with BBr3 to p-bromocalix[4]-arene, which melts above 430 °C. The structure of p-bromocalix[4]arene has been established by the criteria discussed in this article except x-ray crystallography. p-Chlorocalix[4]arene, claimed to be the product of the synthesis illustrated in Scheme 4 97), is reported to melt at 239–242 °C. The enormous difference in melting points between the p-bromo and p-chloro compounds casts considerable doubt on the structure of the p-chloro compound.Google Scholar
  125. 125.
    Lin, L. G.: unpublished observationsGoogle Scholar
  126. 126.
    Gutsche, C. D., Levine, J. A.: J. Am. Chem. Soc. 104, 2652 (1982)CrossRefGoogle Scholar
  127. 127.
    Hagan, M.: Clathrate Inclusion Compounds, Reinhold, New York, 1962Google Scholar
  128. 128.
    Andreetti, G. D.: Internat. Symp. on Clathrate Compounds and Molecular Inclusion Phenomena, Jackranka/Poland, 1980; quoted in ref. 32)Google Scholar
  129. 129.
    Uzawa, J., Zushi, S., Kodama, Y., Fukuda, Y., Nishihata, K., Umemura, A., Nishio, M., Hirota, M.: Bull. Chem. Soc. Japan 53, 3623 (1980)Google Scholar
  130. 130.
    MacNicol, D. D., McKendrick, J. J., Wilson, D. R.: Chem. Soc. Rev. 7, 65 (1978)CrossRefGoogle Scholar
  131. 131.
    Hilgenfeld, R., Saenger, W.: Angew. Chem. Suppl. 1690 (1982)Google Scholar
  132. 132.
    Andreetti, G. D., Mangia, A., Pochini, A., Ungaro, R.: Abstr. 2nd Internat. Symposium on Clathrate Compounds and Molecular Inclusion Phenomena, Parma/Italy, 1982, p. 42Google Scholar
  133. 133.
    Smolková-Keulemansová, E., Feltl, L.: ibid., p. 45Google Scholar
  134. 134.
    Schubert, H., Agatha, G.: Dermatosen im Beruf und Umwelt 27, 49 (1979)Google Scholar
  135. 135.
    We are indebted to Professor Barry Commoner for making available the testing facilities of the Center for the Study of Biological Systems, Washington University, St Louis, Mo.Google Scholar
  136. 136.
    Beaver, D. J., Shumard, R. S., Stoffel, P. J.: J. Am. Chem. Soc. 75, 5579 (1953)CrossRefGoogle Scholar
  137. 137.
    Hakimelahi, G. H., Moshfegh, A. A.: Helv. Chim. Acta 64, 599 (1981)CrossRefGoogle Scholar
  138. 138.
    A representative but not inclusive list of references includes: (a) D'Arcy Hart, P., Payne, S. N.: Brit. J. Pharmacol. 43, 190 (1971)Google Scholar
  139. 138.(b)
    D'Arcy Hart, P., Gordon, A. H.: Nature 222, 672 (1969)PubMedGoogle Scholar
  140. 138.(c)
    Niffenegger, J., Youmans, G. P.: Brit. J. Exptl. Pathol. 41, 403 (1960)Google Scholar
  141. 138.(d)
    Fulton, J. D.: Nature 187, 1129 (1960)Google Scholar
  142. 138.(e)
    Depamphilis, M. L.: J. Bact., 105, 1184 (1971)PubMedGoogle Scholar
  143. 138.(f)
    Allwood, M. C.: Microbios 7, 209 (1973)PubMedGoogle Scholar
  144. 139.
    A representative but non-inclusive list of references includes: (a) Carter, R. L., Birbeck, M. S. C., Stock, J. A.: Int. J. Cancer 7, 32 (1971)Google Scholar
  145. 139.(b)
    Miller, G. W., Janicki, B. W.: Cancer Chem. 52, 243 (1968)Google Scholar
  146. 139.(c)
    Franchi, G., Morasca, L., Reyers-Delgi-Innocenti, I., Garattini, S.: Europ. J. Cancer 7, 535 (1971)Google Scholar
  147. 139.(d)
    Rosso, R., Donelli, M. G., Franchi, G., Garattini, S.: Cancer Chemotherapy Rpt. 54, 79 (1970)Google Scholar
  148. 140.
    Vögtle, F., Sieger, H., Müller, W. M.: Host Guest Complex Chemistry I, in Topics in Current Chemistry, Springer-Verlag, Berlin, 1981, p. 107Google Scholar
  149. 141.
    Sujeeth, P. K.: unpublished observationsGoogle Scholar

Copyright information

© Springer-Verlag 1984

Authors and Affiliations

  • C. David Gutsche
    • 1
  1. 1.Department of ChemistryWashington UniversitySt. LouisUSA

Personalised recommendations