Advertisement

Carbonimidoyl Dihalides

  • Henri Ulrich

Abstract

In 1874 Sell and Zierold (137) obtained phenylcarbonimidoyl dichloride I in the reaction of phenylisothiocyanate II with chlorine. Several years later, Nef (108,109)prepared carbonimidoyl dichlorides by addition of chlorine to isocyanides, such as phenyl isocyanide III. This relationship between I and isocyanides (isonitriles) led to the frequently used term isocyanide dichlorides for the compounds under discussion.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    Allenstein, E., and Schmidt, A., Ber. 97, 1286 (1964).Google Scholar
  2. 2.
    Alimov, P., and Lerkova, L. N., Izv. Akad. Nauk SSR. Ser. Khim. 932 (1964)Google Scholar
  3. Alimov, P., and Lerkova, L. N., Chem. Ahstr. 61. 5502 (1964).Google Scholar
  4. 3.
    Anders, B., Kühle, E., and Malz, H., German Pat. 1,173,469 (1964)Google Scholar
  5. Anders, B., Kühle, E., and Malz, H., Chem. Ahstr. 61, 11892 (1964).Google Scholar
  6. 4.
    Anders, B., and Kühle, E., German Pat. 1,178,422 (1964)Google Scholar
  7. Anders, B., and Kühle, E., Chem. Abstr. 61, 14539 (1964).Google Scholar
  8. 5.
    Anders, B., and Kühle, E., Angew. Chem. Intern. Ed. 4, 430 (1965).CrossRefGoogle Scholar
  9. 6.
    Anders, B., Federmann, M., and Kühle, E., German Pat. 1,195,750 (1965)Google Scholar
  10. Anders, B., Federmann, M., and Kühle, E., Chem. Abstr. 63, 11371 (1965).Google Scholar
  11. 7.
    Anders, B., Kühle, E., and Dickore, K., United States Pat. 3,299,134 (1967).Google Scholar
  12. 8.
    Antia, M. B., and Pandit, M. I., Vikram, J. Vikram Univ. 5, 106 (1961)Google Scholar
  13. Antia, M. B., and Pandit, M. I., Chem. Abstr. 59, 3798 (1963).Google Scholar
  14. 9.
    Attaway, J. A., Groth, R. H., and Bigelow, L. A., J. Am. Chem. Soc. 81, 3599 (1959).CrossRefGoogle Scholar
  15. 10.
    Bacon, R. G. R., Irwin, R. S., Pollock, J. M., and Pullin, A. D. E., J. Chem. Soc. 764 (1958).Google Scholar
  16. 11.
    Banks, R. E., Haszeldine, R. N., and Sutcliffe, H., J. Chem. Soc. 4066 (1964).Google Scholar
  17. 12.
    Barr, D. A., and Haszeldine, R. N., J. Chem. Soc. 3428 (1956).Google Scholar
  18. 13.
    Barr, D. A., Haszeldine, R. N., and Willis, C. J., J. Chem. Soc. 1351 (1961).Google Scholar
  19. 14.
    Bly, R. S., Perkins, G. A., and Lewis, W. L., J. Am. Chem. Soc. 44, 2896 (1922).CrossRefGoogle Scholar
  20. 15.
    Brintzinger, H., Pfannstiel, K., and Koddebusch, H., Ber. 82, 389 (1949).Google Scholar
  21. 16.
    Burkhardt, J., Feinauer, R., Gulbins, E., and Hamann, K., Ber. 99, 1912 (1966).Google Scholar
  22. 17.
    Degener, E., Holtschmidt, H., and Schmelzer, H. G., German Pat. 1,163,803 (1964)Google Scholar
  23. Degener, E., Holtschmidt, H., and Schmelzer, H. G., Chem. Abstr. 60, 14432 (1964).Google Scholar
  24. 18.
    Dennstedt, M., Ber. 13, 228 (1880).CrossRefGoogle Scholar
  25. 19.
    Derkach, G. I., and Liptuga, N. I., Zh. Obshch. Khim. 36, 461 (1966)Google Scholar
  26. Derkach, G. I., and Liptuga, N. I., Chem. Abstr. 65, 634 (1966).Google Scholar
  27. 20.
    Dickore, K., and Kühle, E., Angew. Chem. Intern. Ed. 4, 430 (1965).CrossRefGoogle Scholar
  28. 20a.
    Dobbie, R. C., and Emeleus, H. J., J. Chem. Soc. A, 933 (1966).CrossRefGoogle Scholar
  29. 21.
    Douglass, I. B., and Johnson, T. B., J. Am. Chem. Soc. 60, 1486 (1938).CrossRefGoogle Scholar
  30. 21a.
    Diekmann, J., J. Org. Chem. 28, 2933 (1963).Google Scholar
  31. 22.
    Dresdner, R. D., J. Am. Chem. Soc. 79, 69 (1957).CrossRefGoogle Scholar
  32. 23.
    Dresdner, R. D., Tlumac, F. N., and Young, Y. A., J. Am. Chem. Soc. 82, 5831 (1960).CrossRefGoogle Scholar
  33. 24.
    Dyson, G. M., and Harrington, T., J. Chem. Soc. 191 (1940).Google Scholar
  34. 25.
    Dyson, G. M., and Harrington, T., J. Chem. Soc. 150 (1942).Google Scholar
  35. 26.
    Dyson, G. M., and Harrington, T., J. Chem. Soc. 374 (1942).Google Scholar
  36. 27.
    Eue, L., Hack, H., Kühle, E., and Holtschmidt, H., Belgian Pat. 659,017 (1965)Google Scholar
  37. Eue, L., Hack, H., Kühle, E., and Holtschmidt, H., Chem. Abstr. 64, 1970 (1966).Google Scholar
  38. 28.
    Farbenfabriken Bayer, A. G., British Pat. 888,646 (1962)Google Scholar
  39. Farbenfabriken Bayer, A. G., Chem. Abstr. 57, 13696 (1962).Google Scholar
  40. 29.
    Farbenfabriken Bayer, A. G., British Pat. 981,107 (1965)Google Scholar
  41. Farbenfabriken Bayer, A. G., Chem. Abstr. 62, 11094 (1965).Google Scholar
  42. 30.
    Farbenfabriken Bayer, A. G., British Pat. 1,022,040 (1966).Google Scholar
  43. 31.
    Farbenfabriken Bayer, A.G., Netherlands Appl. 6,409,122 (1965)Google Scholar
  44. Farbenfabriken Bayer, A. G., Chem. Abstr. 63, 8327 (1965).Google Scholar
  45. 32.
    Farbenfabriken Bayer, A.G., Netherlands Appl. 6,414,309 (1965)Google Scholar
  46. Farbenfabriken Bayer, A. G., Chem. Abstr. 64, 2016 (1966).Google Scholar
  47. 33.
    Farbenfabriken Bayer, A.G., Netherlands Appl. 6,516,261 (1966)Google Scholar
  48. Farbenfabriken Bayer, A. G., Chem. Abstr. 65, 18567 (1966).Google Scholar
  49. 34.
    Fawcett, F. S., Tullock, C. W., and Coffman, D. D., J. Am. Chem. Soc. 84, 4275 (1962).CrossRefGoogle Scholar
  50. 35.
    Fujisawa, T., Tamura, Y., and Mukaiyama, T., Bull. Chem. Soc. Japan 37, 793 (1964)CrossRefGoogle Scholar
  51. Fujisawa, T., Tamura, Y., and Mukaiyama, T., Chem. Abstr. 61, 16166 (1964).Google Scholar
  52. 36.
    Gauss, W., and Kühle, E., French Pat. 1,363,063 (1964)Google Scholar
  53. Gauss, W., and Kühle, E., Chem. Abstr. 62, 2763 (1965).Google Scholar
  54. 37.
    Gompper, R., and Kunz, R., Ber. 99, 2900 (1966).Google Scholar
  55. 37a.
    Green, M., and Tipping, A. E., J. Chem. Soc. 5774 (1965).Google Scholar
  56. 38.
    Gross, H., Rusche, J., and Bornowski, H., Ann. 675, 142 (1964).Google Scholar
  57. 39.
    Guillemard, H., Ann. Chim. [8] 14, 224 (1904).Google Scholar
  58. 40.
    Gulbins, K., and Hamann, K., Angew. Chem. 73, 434 (1961).Google Scholar
  59. 41.
    Gumpert, F., J. prakt. Chem. 31, 119 (1885).CrossRefGoogle Scholar
  60. 42.
    Gysin, H., Knuesli, E., and Rumpf, J., United States Pat. 3,053,843 (1962)Google Scholar
  61. Gysin, H., Knuesli, E., and Rumpf, J., Chem. Abstr. 58, 6846 (1963).Google Scholar
  62. 43.
    Hagedorn, I., Etling, H., and Lichtel, E., Ber. 99, 520 (1966).Google Scholar
  63. 44.
    Hantzsch, A., and Mai, L., Ber. 28, 977 (1895).CrossRefGoogle Scholar
  64. 45.
    Hauptschein, M., Braid, M., and Lawlor, F. E., J. Org. Chem. 23, 323 (1958).CrossRefGoogle Scholar
  65. 46.
    Hauptschein, M., United States Pat. 2,966,517 (1960)Google Scholar
  66. Hauptschein, M., Chem. Abstr. 55, 10480 (1961).Google Scholar
  67. 47.
    Helmers, O., Ber. 20, 786 (1887).CrossRefGoogle Scholar
  68. 48.
    Homeyer, B., Kühle, E., and Malz, H., German Pat. 1,147,797 (1963)Google Scholar
  69. Helmers, O., Chem. Abstr. 59, 1044 (1963).Google Scholar
  70. 49.
    Holtschmidt, H., Angew. Chem. Intern. Ed. 1, 632 (1962).CrossRefGoogle Scholar
  71. 50.
    Holtschmidt, H., German Pat. 1,141,278 (1962)Google Scholar
  72. Holtschmidt, H., Chem. Abstr. 59, 456 (1963).Google Scholar
  73. 51.
    Holtschmidt, H., Belgian Pat. 617,414 (1962)Google Scholar
  74. Holtschmidt, H., Chem. Abstr. 58, 12430 (1963).Google Scholar
  75. 52.
    Holtschmidt, H., and Zecher, W., Belgian Pat. 622,381 (1962)Google Scholar
  76. Holtschmidt, H., Chem. Abstr. 59, 11526 (1963).Google Scholar
  77. 53.
    Holtschmidt, H., and Zecher, W., Belgian Pat. 622,382 (1962)Google Scholar
  78. Holtschmidt, H., Chem. Abstr. 59, 11534 (1963).Google Scholar
  79. 54.
    Holtschmidt, H., United States Pat. 3,190,918 (1965).Google Scholar
  80. 54a.
    Holtschmidt, H., Degener, E., and Schmelzer, H. G., Ann. 701, 107 (1967).Google Scholar
  81. 55.
    Ivanova, Zh. M., Derkach, G. I., and Kirsanova, N. A., Zh. Obshch. Khim. 34, 3516 (1964)Google Scholar
  82. Ivanova, Zh. M., Derkach, G. I., and Kirsanova, N. A., Chem. Abstr. 62, 2725 (1965).Google Scholar
  83. 56.
    Ivanova, Zh. M., Kirsanova, N. A., and Derkach, G. I., Zh. Organ. Khim. 1, 2186 (1965)Google Scholar
  84. Ivanova, Zh. M., Kirsanova, N. A., and Derkach, G. I., Chem. Abstr. 64, 11123 (1966).Google Scholar
  85. 56a.
    Jarovenko, N. N., Motomyi, S. P., and Kirenskaja, L. I., Zh. Obshch. Khim. 29, 3789 (1959).Google Scholar
  86. 57.
    Jentzsch, W., Ber. 97, 1361 (1964).Google Scholar
  87. 58.
    Jentzsch, W., Ber. 97, 2755 (1964).Google Scholar
  88. 59.
    Johnson, H. W., Jr., and Daughhetee, P. H., Jr., J. Org. Chem. 29, 246 (1964).CrossRefGoogle Scholar
  89. 60.
    Jungermann, E., and Smith, F. W., J. Am. Oil Chemist’s Soc. 36, 388 (1959)CrossRefGoogle Scholar
  90. Jungermann, E., and Smith, F. W., Chem. Abstr. 54, 289 (1960).Google Scholar
  91. 61.
    Kaji, A., and Miyazaki, K., Nippon Kagaku Zasshi, 87, 727 (1966)CrossRefGoogle Scholar
  92. Kaji, A., and Miyazaki, K., Chem. Abstr. 65, 15255 (1966).Google Scholar
  93. 62.
    Kauer, J. C., and Sheppard, W. A., J. Org. Chem. 32, 3580 (1967).CrossRefGoogle Scholar
  94. 63.
    Kaufmann, H. P., and Liepe, J., Ber. 57, 923 (1924).Google Scholar
  95. 64.
    Kirsanov, A. V., Derkach, G. I., and Liptuga, N. I., Zh. Otshch. Khim. 34, 2812 (1964)Google Scholar
  96. Kirsanov, A. V., Derkach, G. I., and Liptuga, N. I., Chem. Abstr. 61, 14514 (1964).Google Scholar
  97. 65.
    Klauke, E., and Kühle, E., Belgian Pat. 632,365 (1963)Google Scholar
  98. Klauke, E., and Kühle, E., Chem. Abstr. 61, 6952 (1964).Google Scholar
  99. 66.
    Klauke, E., and Kühle, E., German Pat. 1,170,414 (1964).Google Scholar
  100. 67.
    Klauke, E., Angew. Chem. Intern. Ed. 5, 848 (1966).CrossRefGoogle Scholar
  101. 68.
    Knunyants, I. L., Bykhovskaya, E. G., and Frosin, V. N., Doklady Akad. Nauk SSSR 132, 357 (1960)Google Scholar
  102. Knunyants, I. L., Bykhovskaya, E. G., and Frosin, V. N., Chem. Abstr. 54, 20841 (1960).Google Scholar
  103. 69.
    Kodama, Y., Yuki Gosei Kagaku Kyokai Shi 21, 525 (1963)CrossRefGoogle Scholar
  104. Kodama, Y., Chem. Abstr. 59, 8748 (1963).Google Scholar
  105. 70.
    Kodama, Y., and Sekiba, T., Yuki Gosei Kagaku Kyokai Shi 21, 788 (1963)CrossRefGoogle Scholar
  106. Kodama, Y., and Sekiba, T., Chem. Abstr. 59, 15290 (1963).Google Scholar
  107. 71.
    Kodama, Y., and Sekiba, T., Yuki Gosei Kagaku Kyokai Shi 22, 467 (1964)CrossRefGoogle Scholar
  108. Kodama, Y., and Sekiba, T., Chem. Abstr. 61, 7015 (1964).Google Scholar
  109. 72.
    Kodama, Y., Sekiba, T., and Ho, T., Yuki Gosei Kagaku Kyokai Shi 22, 567 (1964)CrossRefGoogle Scholar
  110. Kodama, Y., Sekiba, T., and Ho, T., Chem. Abstr. 61, 9160 (1964).Google Scholar
  111. 73.
    Kodama, Y., Sekiba, T., and Kato, M., Yuki Gosei Kagaku Kyokai Shi 22, 749 (1964)CrossRefGoogle Scholar
  112. Kodama, Y., Sekiba, T., and Kato, M., Chem. Abstr. 61, 12002 (1964).Google Scholar
  113. 74.
    Kodama, Y., Yuki Gosei Kagaku Kyokai 23, 57 (1965)CrossRefGoogle Scholar
  114. Kodama, Y., Chem. Abstr. 62, 9132 (1965).Google Scholar
  115. 75.
    Kodama, Y., and Sekiba, T., Japanese Pat. 11,389 (1965)Google Scholar
  116. Kodama, Y., and Sekiba, T., Chew. 63, 13293 (1965).Google Scholar
  117. 76.
    Kodama, Y., and Sekiba, T., Japanese Pat. 20,394 (1965)Google Scholar
  118. Kodama, Y., and Sekiba, T., Chem. Abstr. 63, 18124 (1965).Google Scholar
  119. 77.
    Kodama, Y., and Sekiba, T., Japanese Pat. 20,395 (1965)Google Scholar
  120. Kodama, Y., and Sekiba, T., Chem. Abstr. 63, 18124 (1965).Google Scholar
  121. 78.
    Kodama, Y., Sekiba, T., and Kato, M., Japanese Pat. 28,098 (1965)Google Scholar
  122. Kodama, Y., and Sekiba, T., Chem. Abstr. 64, 11231 (1966).Google Scholar
  123. 79.
    Kodama, Y., and Shinohara, S., Japanese Pat. 28,099 (1965)Google Scholar
  124. Kodama, Y., and Sekiba, T., Chem. Abstr. 64, 11231 (1966).Google Scholar
  125. 80.
    Kodama, Y., and Shinohara, S., Japanese Pat. 28,100 (1965)Google Scholar
  126. Kodama, Y., and Sekiba, T., Chem. Abstr. 64, 11231 (1966).Google Scholar
  127. 81.
    Kodama, Y., Sekiba, T., and Kato, M., Japanese Pat. 28,101 (1965)Google Scholar
  128. Kodama, Y., and Sekiba, T., Chem. Abstr. 64, 11232 (1966).Google Scholar
  129. 82.
    Kodama, Y., and Sekiba, T., Japanese Pat. 430 (1966)Google Scholar
  130. Kodama, Y., and Sekiba, T., Chem. Abstr. 64, 11230 (1966).Google Scholar
  131. 83.
    Kodama, Y., and Sekiba, T., Japanese Pat. 431 (1966)Google Scholar
  132. Kodama, Y., and Sekiba, T., Chem. Abstr. 64, 11231 (1966).Google Scholar
  133. 84.
    Kühle, E., German Pat. 1,094,737 (1960)Google Scholar
  134. Kodama, Y., and Sekiba, T., Chem. Abstr. 55, 25860 (1961).Google Scholar
  135. 85.
    Kühle, E., and Wegler, R., German Pat. 1,126,371 (1959)Google Scholar
  136. Kodama, Y., and Sekiba, T., Chem. Abstr. 51. 11102 (1962).Google Scholar
  137. 86.
    Kühle, E., Angew. Chem. Intern. Ed. 1, 647 (1962).CrossRefGoogle Scholar
  138. 87.
    Kühle, E., German Pat. 1,126,380 (1962).Google Scholar
  139. 88.
    Kühle, E., Eue, L., and Bayer, O., German Pat. 1,137,000 (1962).Google Scholar
  140. 89.
    Kühle, E., and Sasse, K., German Pat. 1,174,772 (1964)Google Scholar
  141. Kühle, E., and Sasse, K., Chem. Abstr. 61, 10627 (1964).Google Scholar
  142. 90.
    Kühle, E., German Pat. 1,192,189 (1965)Google Scholar
  143. Kühle, E., Chem. Abstr. 63, 6918 (1965).Google Scholar
  144. 91.
    Kühle, E., United States Pat. 3,235,580 (1966).Google Scholar
  145. 92.
    Kühle, E., and Eue, L., United States Pat. 3,267,097 (1966)Google Scholar
  146. Kühle, E., Chem. Abstr. 65, 13729 (1966).Google Scholar
  147. 93.
    Kühle, E., and Anders, B., French Pat. 1,405,732 (1965)Google Scholar
  148. Kühle, E., Chem. Abstr. 64, 9603 (1966).Google Scholar
  149. 94.
    Kühle, E., Belgian Pat. 660,171 (1965)Google Scholar
  150. Kühle, E., Chem. Abstr. 64, 603 (1966).Google Scholar
  151. 95.
    Kühle, E., and Anders, B., German Pat. 1,224,306 (1966)Google Scholar
  152. Kühle, E., Chem. Abstr. 65, 18536 (1966).Google Scholar
  153. 95a.
    Kühle, E., Anders, B., and Zumach, G., Angew. Chem. 79, 663 (1967).CrossRefGoogle Scholar
  154. 96.
    Lonza, Ltd., British Pat. 1,052,567 (1966)Google Scholar
  155. Lonza, Ltd., Chem. Abstr. 66, 55525 (1967).Google Scholar
  156. 97.
    Makarov, S. P., Shpanskii, V. A., Ginsburg, V. A., Shchekotikhin, A. I., Filatov, A. S., Martynova, L. L., Parlovskaya, I. V., Golovaneva, A. F., and Yakubovich, A. Y., Dokl. Akad. Nauk SSSR 142, 596 (1962)Google Scholar
  157. Makarov, S. P., Shpanskii, V. A., Ginsburg, V. A., Shchekotikhin, A. I., Filatov, A. S., Martynova, L. L., Parlovskaya, I. V., Golovaneva, A. F., and Yakubovich, A. Y., Chem. Abstr. 57, 4528 (1962).Google Scholar
  158. 98.
    Malinovski, M. S., Sci. Records Gorky State Univ. 7, 29 (1939)Google Scholar
  159. Malinovski, M. S., Chem. Abstr. 35, 442 (1941).Google Scholar
  160. 99.
    Malz, H., Kühle, E., and Bayer, O., German Pat. 1,138,389 (1962).Google Scholar
  161. 100.
    Malz, H., Holtschmidt, H., Kühle, E., and Bayer, O., Belgian Pat. 627,486 (1963)Google Scholar
  162. Malz, H., Holtschmidt, H., Kühle, E., and Bayer, O., Chem. Abstr. 60, 10557 (1964).Google Scholar
  163. 101.
    Malz, H., and Kühle, E., German Pat. 1,158,501 (1963)Google Scholar
  164. Malz, H., and Kühle, E., Chem. Abstr. 60, 6795 (1964).Google Scholar
  165. 102.
    Mitsch, R. A., and Ogden, P. H., J. Org. Chem. 31, 3833 (1966).CrossRefGoogle Scholar
  166. 103.
    Moeckel, K., and Gehlen, H., Z. Chem. 4, 388 (1964)CrossRefGoogle Scholar
  167. Moeckel, K., and Gehlen, H., Chem. Abstr. 62, 1647 (1965).Google Scholar
  168. 104.
    Mukaiyama, T., Fujisawa, T., and Hyugaji, T., Bull. Chem. Soc. Japan 35, 687 (1962).CrossRefGoogle Scholar
  169. 105.
    Mukaiyama, T., Fujisawa, T., and Mitsunobo, O., Bull. Chem. Soc. Japan 35, 1104 (1962).CrossRefGoogle Scholar
  170. 106.
    Mukaiyama, T., Fujisawa, T., Nohira, H., and Hyugaji, T., J. Org. Chem. 27, 3337 (1962).CrossRefGoogle Scholar
  171. 107.
    Murphy, D. B., J. Org. Chem. 29, 1613 (1964).CrossRefGoogle Scholar
  172. 108.
    Nef, J. U., Ann. 270, 267 (1892).Google Scholar
  173. 109.
    Nef, J. U., Ann. 280, 291 (1894).Google Scholar
  174. 110.
    Neidlein, R., and Haussmann, W., Angew. Chem. Intern. Ed. 4, 521 (1965).Google Scholar
  175. 111.
    Neidlein, R., and Haussmann, W., Tetrahedron Letters 1753 (1965).CrossRefGoogle Scholar
  176. 112.
    Neidlein, R., and Haussmann, W., Tetrahedron Letters 2423 (1965)Google Scholar
  177. 113.
    Neidlein. R., and Heukelbach. E., Tetrahedron Letters 2665 (1965).CrossRefGoogle Scholar
  178. 114.
    Neidlein, R., and Haussmann, W., Ber. 99, 239 (1966).Google Scholar
  179. 115.
    Neidlein, R., Haussmann, W., and Heukelbach, E., Ber. 99, 1252 (1966).Google Scholar
  180. 116.
    Neidlein, R., and Haussmann, W., Tetrahedron Letters 2217 (1966).CrossRefGoogle Scholar
  181. 117.
    Neidlein, R., and Heukelbach, E., Arch. Pharm. 299, 944 (1966).CrossRefGoogle Scholar
  182. 118.
    Neidlein, R., and Haussmann, W., Z. Naturforsch. 21, 898 (1966).CrossRefGoogle Scholar
  183. 119.
    Oda, R., Hamada, T., Ito, Y., and Okano, M., Bull. Inst. Chem. Res. Kvoto Univ. 44. 227 (1966)Google Scholar
  184. Oda, R., Hamada, T., Ito, Y., and Okano, M., Chem. Ahstr. 66, 37806f (1967).Google Scholar
  185. 120.
    Ottmann, G., and Hooks, H., Angew. Chem. Intern. Ed. 4, 432 (1965).CrossRefGoogle Scholar
  186. 121.
    Ottmann, G., and Hooks, H., J. Org. Chem. 31, 838 (1966).CrossRefGoogle Scholar
  187. 122.
    Ottmann, G., and Hooks, H., Angew. Chem. Intern. Ed. 5, 250 (1966).CrossRefGoogle Scholar
  188. 123.
    Ottmann, G., and Hooks, H., United States Pat. 3,267,144 (1966)Google Scholar
  189. Ottmann, G., and Hooks, H., Chem. Abstr. 65, 20029 (1966).Google Scholar
  190. 124.
    Ottmann, G., and Hooks, H., J. Med. Chem. 9, 962 (1966).PubMedCrossRefGoogle Scholar
  191. 125.
    Pawellek, D., Angew. Chem. Intern. Ed. 5, 845 (1966).CrossRefGoogle Scholar
  192. 125a.
    Pearlson, W. A., and Hals, L. J., United States Pat. 2,643,267 (1950).Google Scholar
  193. 126.
    Pel’kis, P. S., and Dunaevska, T. S., Mem. Inst. Chem. Acad. Sci. Ukrain. SSSR 6, 163 (1940)Google Scholar
  194. Pel’kis, P. S., and Dunaevska, T. S., Chem. Abstr. 34, 5829 (1940).Google Scholar
  195. 127.
    Petrov, K. A., and Neimysheva, A. A., Zh. Obshch. Khim. 29, 2165 (1959)Google Scholar
  196. Petrov, K. A., and Neimysheva, A. A., Chem. Abstr. 54, 10911 (1960).Google Scholar
  197. 128.
    Petrov, K. A., and Neimysheva, A. A., Zh. Obshch. Khim. 29, 2169 (1959)Google Scholar
  198. Petrov, K. A., and Neimysheva, A. A., Chem. Abstr. 54, 10912 (1960).Google Scholar
  199. 129.
    Petrov, K. A., and Neimysheva, A. A., Zh. Obshch. Khim. 29, 2695 (1959)Google Scholar
  200. Petrov, K. A., and Neimysheva, A. A., Chem. Abstr. 54, 10912 (1960).Google Scholar
  201. 130.
    Prandtl, W., and Sennewald, K., Ber. 62, 1764 (1929).Google Scholar
  202. 131.
    Riethman, J., and Wegmüller, H., German Pat. 1,132,559 (1962).Google Scholar
  203. 132.
    Rosen, I., and Stallings, J. P., J. Org. Chem. 25, 1484 (1960).CrossRefGoogle Scholar
  204. 133.
    Sallmann, A., and Pfister, R., German Pat. 1,163,841 (1964)Google Scholar
  205. Sallmann, A., and Pfister, R., Chem. Abstr. 64, 5119 (1966).Google Scholar
  206. 134.
    Sayigh, A. A. R., and Ulrich, H., J. Chem. Soc. 3146 (1963).Google Scholar
  207. 135.
    Schmelzer, H. G., and Degener, E., German Pat. 1,178,437 (1964)Google Scholar
  208. Schmelzer, H. G., and Degener, E., Chem. Abstr. 61, 16081 (1964).Google Scholar
  209. 136.
    Schmidt, E., and Thulke, K., Ann. 663, 46 (1963).Google Scholar
  210. 136a.
    Scott, F. L., and Cronin, D. A., Chem. and Ind. 1757 (1964).Google Scholar
  211. 137.
    Sell, E., and Zierold, G., Ber. 7, 1228 (1874).CrossRefGoogle Scholar
  212. 138.
    Seyferth, D., and Damrauer, R., Tetrahedron Letters 189 (1966).CrossRefGoogle Scholar
  213. 139.
    Sheppard, W. A., J. Am. Chem. Soc. 87, 4338 (1965).CrossRefGoogle Scholar
  214. 140.
    Shipton, G. O., British Pat. 945,855.Google Scholar
  215. Shipton, G. O., Chem. Abstr. 60, 10700 (1964).Google Scholar
  216. 141.
    Smith, P. A. S., and Kalenda, N. W., J. Org. Chem. 23, 1599 (1958).CrossRefGoogle Scholar
  217. 142.
    Smith, W. R., Am. Chem. J. 16, 372 (1894).CrossRefGoogle Scholar
  218. 143.
    Sokolov, S. v., and Mazalov, S. A., and Gerasimov, S. I., Zh. Vses. Khim. Obshchestva im. D. I. Mendeleeva 10, 234 (1965).Google Scholar
  219. 144.
    Tarnow, H., Holtschmidt, H., and Unterstenhoefer, G., German Pat. 1,197,078 (1965)Google Scholar
  220. Tarnow, H., Holtschmidt, H., and Unterstenhoefer, G., Chem. Abstr. 63, 14774 (1965).Google Scholar
  221. 144a.
    Thiele, J., Ber. 26, 2645 (1893).CrossRefGoogle Scholar
  222. 145.
    Thiele, J., Ann. 303, 5770 (1898).Google Scholar
  223. 145a.
    Tscherniak, M., Bull. Soc. Chim. France [2] 30, 185 (1878).Google Scholar
  224. 146.
    Tullock, C. W., Coflfman, D. D., and Mutterties, E. L., J. Am. Chem. Soc. 86, 357 (1964).CrossRefGoogle Scholar
  225. 147.
    Ulrich, H., and Sayigh, A. A. R., Angew. Chem. Intern. Ed. 1, 595 (1962).CrossRefGoogle Scholar
  226. 148.
    Ulrich, H., and Sayigh, A. A. R., J. Chem. Soc. 5558 (1963).Google Scholar
  227. 149.
    Ulrich, H., and Sayigh, A. A. R., Angew. Chem. Intern. Ed. 3, 585 (1964).CrossRefGoogle Scholar
  228. 150.
    Ulrich, H., and Sayigh, A. A. R., J. Org. Chem. 30, 2779 (1965).CrossRefGoogle Scholar
  229. 151.
    Ulrich, H., Cycloaddition Reactions of Heterocumulenes, Academic Press, New York (1967).Google Scholar
  230. 152.
    Warren, W. H., and Wilson, F. R., Ber. 68, 957 (1935).Google Scholar
  231. 153.
    Wellcome Found. Ltd., Belgian Pat. 667,875 (1966)Google Scholar
  232. Wellcome Found. Ltd., Chem. Abstr. 65, 5398 (1966).Google Scholar
  233. 154.
    Yarovenko, N. N., Motornyi, S. P., and Kirenskaya, L. I., Zh. Obshch. Khim. 29, 3789 (1959)Google Scholar
  234. Yarovenko, N. N., Motornyi, S. P., and Kirenskaya, L. I., Chem. Abstr. 54, 19479 (1960).Google Scholar
  235. 155.
    Young, J. A., Simmons, T. C., and Hoffmann, F. W., J. Am. Chem. Soc. 78, 5637 (1956).CrossRefGoogle Scholar
  236. 156.
    Young, J. A., Tsoukalas, S. N., and Dresdner, R. D., J. Am. Chem. Soc. 80, 3604 (1958).CrossRefGoogle Scholar
  237. 157.
    Young, J. A., Durell, W. S., and Dresdner, R. D., Am. Chem. Soc. 81. 1587 (1959).CrossRefGoogle Scholar
  238. 158.
    Young, J. A., Tsoukalas, S. N., and Dresdner, R. D., J. Am. Chem. Soc. 82. 396 (1960).CrossRefGoogle Scholar
  239. 159.
    Young, J. A., and Dresdner, R. D., J. Org. Chem. 28, 833 (1963)CrossRefGoogle Scholar

Copyright information

© Plenum Press 1968

Authors and Affiliations

  • Henri Ulrich
    • 1
  1. 1.Donald S. Gilmore Research LaboratoriesThe Upjohn CompanyNorth HavenUSA

Personalised recommendations