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Abstract

The reaction of substituted carboxylic acid amides with a variety of halogenating agents, such as phosphorus pentachloride, phosphorus pentabromide, thionyl chloride, and carbonyl chloride, produces imidoyl halides or iminium halides, depending upon the structure of the amide. For example, a monosubstituted carboxylic acid amide can react with carbonyl chloride to produce the imidoyl chloride I, or its hydrochloride II, if R’ is aliphatic.

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References

  1. Adams, R., and Wicks, Z. W., J. Am. Chem. Soc. 66, 1315 (1944).

    Article  CAS  Google Scholar 

  2. Akabori, S., and Senoh, J., Bull. Chem. Soc. Japan 14, 166 (1939).

    Article  CAS  Google Scholar 

  3. Albers, H., Oster, R., and Schroeder, H., German Pat. 1,178,052 (1964)

    Google Scholar 

  4. Albers, H., Oster, R., and Schroeder, H., Chem. Abstr. 61, 16080 (1964).

    Google Scholar 

  5. Albright, J. D., Benz, E., Lanzilotti, A. E., and Goldman, L., Chem. Commun. 413 (1965).

    Google Scholar 

  6. Allenstein, E., and Schmidt, A., Ber. 97, 1286 (1964).

    CAS  Google Scholar 

  7. Allenstein, E., and Quis, P., Ber. 97, 1857 (1964).

    CAS  Google Scholar 

  8. Allenstein, E., and Schmidt, A., Ber. 97, 1863 (1964).

    CAS  Google Scholar 

  9. Allenstem, E., and Quis, P., Ber. 97, 3162 (1964).

    Google Scholar 

  10. D’Amico, J. J., Webster, S. T., Campbell, R. H., and Twine, C. E., J. Org. Chem. 30, 3618 (1965).

    Article  Google Scholar 

  11. Anker, R. M., and Cook, A. H., J. Chem. Soc. 489 (1944).

    Google Scholar 

  12. Arbuzov, A. E., Shishkin, V. E., and Tyulenev, S. S., Zh. Organ. Khim. 1, 1442 (1965).

    CAS  Google Scholar 

  13. Arnold, Z., and Sorm, F., Coll. Czech. Chem. Commun. 23, 452 (1958).

    Article  Google Scholar 

  14. Arnold, Z., and Zemlicka, J., Coll. Czech. Chem. Commun. 24, 786 (1959).

    Article  CAS  Google Scholar 

  15. Arnold, Z., and Zemlicka, J., Coll. Czech. Chem. Commun. 24, 2378 (1959).

    Article  CAS  Google Scholar 

  16. Arnold, Z., and Zemlicka, J., Coll. Czech. Chem. Commun. 24, 2385 (1959).

    Article  CAS  Google Scholar 

  17. Arnold, Z., Coll. Czech. Chem. Commun. 24, 4048 (1959).

    Article  CAS  Google Scholar 

  18. Arnold, Z., and Zemlicka, J., Coll. Czech. Chem. Commun. 25, 1302 (1960).

    Article  CAS  Google Scholar 

  19. Arnold, Z., Coll. Czech. Chem. Commun. 25, 1308 (1960).

    Article  CAS  Google Scholar 

  20. Arnold, Z., Coll. Czech. Chem. Commun. 25. 1313 (1960).

    Article  CAS  Google Scholar 

  21. Arnold, Z., and Zemlicka, J., Coll. Czech. Chem. Commun. 25, 1318 (1960).

    Article  CAS  Google Scholar 

  22. Arnold, Z., Coll. Czech. Chem. Commun. 26, 1113 (1961).

    Article  CAS  Google Scholar 

  23. Arnold, Z., Coll. Czech. Chem. Commun. 26, 1723 (1961).

    Article  CAS  Google Scholar 

  24. Arnold, Z., and Holy, A., Coll. Czech. Chem. Commun. 26, 3059 (1961).

    Article  CAS  Google Scholar 

  25. Arnold, Z., Angew. Chem. 73, 176 (1961).

    Google Scholar 

  26. Arnold, Z., and Holy, A., Coll. Czech. Chem. Commun. 27, 2886 (1962).

    Article  CAS  Google Scholar 

  27. Arnold, Z., Coll Czech. Chem. Commun. 28, 863 (1962).

    Article  Google Scholar 

  28. Arnold, Z., Coll. Czech. Chem. Commun. 28, 2047 (1963).

    Article  CAS  Google Scholar 

  29. Arnold, Z., and Kornilov, M., Coll. Czech. Chem. Commun. 29, 645 (1964).

    Article  CAS  Google Scholar 

  30. Arnold, Z., and Holy, A., Coll. Czech. Chem. Commun. 30, 47 (1965).

    Article  CAS  Google Scholar 

  31. Arnold, Z., Coll. Czech. Chem. Commun. 30, 2783 (1965).

    Article  CAS  Google Scholar 

  32. Badger, G. M., Elix, J. A., and Lewis, G. E., Austr. J. Chem. 19, 1477 (1966).

    Article  CAS  Google Scholar 

  33. Bayer, O., Houben-Weyl, Methoden der Organischen Chemie, Fourth Edition, Vol. 7, Part 1, G. Thieme, Stuttgart (1954), p. 29.

    Google Scholar 

  34. Behringer, H., Hauser, L., and Kohl, K., Ber. 92, 910 (1959).

    CAS  Google Scholar 

  35. Behringer, H., and Weber, D., Ann. 682, 197 (1965).

    Google Scholar 

  36. Bellefontaine, A., Lorenz, H., and Wizinger, R., Helv. Chim. Acta 28, 600 (1945).

    Article  Google Scholar 

  37. Bernthsen, A., Ber. 10, 1238 (1877).

    Article  Google Scholar 

  38. Beyer, K. H., and Eilingsfeld, H., German Pat. 1,110,625 (1961).

    Google Scholar 

  39. Biltz, H., Ann. 25, 2533 (1892).

    Google Scholar 

  40. Bodendorf, K., and Mayer, R., Ber. 98, 3565 (1965).

    CAS  Google Scholar 

  41. Böhme, H., Hartke, K., and Müller, A., Ber. 96, 607 (1963).

    Google Scholar 

  42. Böshagen, H., Ber. 99, 2566 (1966).

    Google Scholar 

  43. Bosshard, H. H., Mory, R., Schmid, M., and Zollinger, H., Helv. Chim. Acta 41, 1653 (1959).

    Article  Google Scholar 

  44. Bosshard, H. H., and Zollinger, H., Helv. Chim. Acta 42, 1659 (1959).

    Article  CAS  Google Scholar 

  45. Brace, N. O., J. Org. Chem. 28, 3093 (1963).

    Article  CAS  Google Scholar 

  46. Brannock, K. C., and Burpitt, R. D., J. Org. Chem. 30, 2564 (1965).

    Article  Google Scholar 

  47. Braun, J. v., Ber. 37, 2678 (1904).

    Article  CAS  Google Scholar 

  48. Braun, J. v., Ber. 37, 2812 (1904).

    Article  Google Scholar 

  49. Braun, J. v., Ber. 37, 2915 (1904).

    Article  Google Scholar 

  50. Braun, J. v., Ber. 37, 3210 (1904).

    Article  Google Scholar 

  51. Braun, J. v. and Müller, C., Ber. 39, 2018 (1906).

    Article  Google Scholar 

  52. Braun, J. v., and Sobecki, W., Ber. 44, 1464 (1911).

    Article  Google Scholar 

  53. Braun, J. v., Ber. 55, 3165 (1922).

    Google Scholar 

  54. Braun, J. v., Ber.449, 249 (1926).

    Google Scholar 

  55. Braun, J. v., Ber. 59, 1444 (1926).

    Google Scholar 

  56. Braun, J. v., Jostes, F., and Heymons, A., Ber. 60, 92 (1927).

    Google Scholar 

  57. Braun, J. v., Jostes, F., and Münch, W., Ann. 453, 113 (1927).

    CAS  Google Scholar 

  58. Braun, J. v., and Heymons, A., Ber. 62, 409 (1929).

    Google Scholar 

  59. Braun, J. v., and Silvermann, H., Ber. 63, 498 (1930).

    Google Scholar 

  60. Braun, J. v., and Heymons, A., Ber. 63, 502 (1930).

    Google Scholar 

  61. Braun, J. v., and Heymons, A., Ber. 63, 3191 (1930).

    Google Scholar 

  62. Braun, J. v., and Rudolph, W., Ber. 64, 2265 (1931).

    Google Scholar 

  63. Braun, J. v., and Weissbach, K., Ber. 65, 1574 (1932).

    Google Scholar 

  64. Braun, J. v., and Rudolph, W., Ber. 67, 269 (1934).

    Google Scholar 

  65. Braun, J. v., and Pinkernelle, W., Ber. 67, 1218 (1934).

    Google Scholar 

  66. Braun, J. v., and Rudolph, W., Ber. 67, 1735 (1934).

    Google Scholar 

  67. Braun, J. v., and Rudolph, W., Ber. 67, 1762 (1934).

    Google Scholar 

  68. Braun, J. v., Angew. Chem. 47, 611 (1934).

    Article  Google Scholar 

  69. Braun, J. v., and Ostermayer, H., Ber. 70, 1002 (1937).

    Google Scholar 

  70. Braun, J. v., and Kurtz, P., Ber. 70, 1009 (1937).

    Google Scholar 

  71. Braun, J. v., and Rudolph, W., Ber. 74, 264 (1941).

    Google Scholar 

  72. Bredereck, H., Gompper, R., Klemm, K., and Rempfer, H., Ber. 92, 837 (1959).

    CAS  Google Scholar 

  73. Bredereck, H., Gompper, R., and Klemm, K., Ber. 92, 1456 (1959).

    CAS  Google Scholar 

  74. Bredereck, H., and Bredereck, K., Ber. 94, 2278 (1961).

    CAS  Google Scholar 

  75. Bredereck, H., and Simchen, G., Angew. Chem. Intern. Ed. 2, 738 (1963).

    Article  Google Scholar 

  76. Bredereck, H., Effenberger, F., and Simchen, G., Ber. 97, 1403 (1964).

    CAS  Google Scholar 

  77. Bredereck, K., and Richter, R., Ber. 98, 131 (1965).

    CAS  Google Scholar 

  78. Bredereck, H., Simchen, G., and Santos, A. A., Ber. 100, 1344 (1967).

    CAS  Google Scholar 

  79. Brown, M., United States Pat. 3,214,412 (1965)

    Google Scholar 

  80. Brown, M., Chem. Abstr. 64, 3542 (1966).

    Google Scholar 

  81. Brownell, W., and Weston, A., J. Am. Chem. Soc. 73, 4971 (1951).

    Article  CAS  Google Scholar 

  82. Buijle, R., Halleux, A., and Viehe, H. G., Angew. Chem. Intern. Ed. 5, 584 (1966).

    Article  CAS  Google Scholar 

  83. Busch, M., and Fleischmann, M., Ber. 43, 2553 (1910).

    Article  CAS  Google Scholar 

  84. Buu-Hoi, N. P., and Hoan, N., J. Am. Chem. Soc. 73, 98 (1951).

    Article  CAS  Google Scholar 

  85. Buu-Hoi, N. P., and Hoan, N., J. Org. Chem. 16, 874 (1951).

    Article  CAS  Google Scholar 

  86. Buu-Hoi, N. P., and Hoan, N., J. Org. Chem. 16, 1327 (1951).

    Article  CAS  Google Scholar 

  87. Buu-Hoi, N. P., and Hoan, N., J. Chem. Soc. 1834 (1951).

    Google Scholar 

  88. Campaigne, E., and Archer, L., J. Am. Chem. Soc. 75, 989 (1953).

    Article  CAS  Google Scholar 

  89. Chapman, A. W., J. Chem. Soc. 121, 1676 (1922).

    Article  CAS  Google Scholar 

  90. Ciba, British Pat. 870,454 (1961)

    Google Scholar 

  91. Chapman, A. W., Chem. Abstr. 56, 11421 (1962).

    Google Scholar 

  92. Ciba, French Pat. 1,181,605 (1959).

    Google Scholar 

  93. Coleman, G. H., and Pyle, R. E., Am. Chem. Soc. 68, 2007 (1947).

    Google Scholar 

  94. Cramer, F., and Baer, K., Ber. 93, 1233 (1960).

    Google Scholar 

  95. Cramer, F., Rittner, S., Reinhard, W., and Desai, P., Ber. 99, 2252 (1966).

    CAS  Google Scholar 

  96. Curtin, D. Y., and Miller, L. L., Tetrahedron Letters 1869 (1965).

    Google Scholar 

  97. Dallacker, F., and Eschelbach, F. E., Ann. 689, 171 (1965).

    CAS  Google Scholar 

  98. Dallacker, F., and Kern, J., Ber. 99, 3830 (1966).

    CAS  Google Scholar 

  99. Decombe, J., and Verry, C., Compte Rend. 256, 5156 (1963).

    CAS  Google Scholar 

  100. Degener, E., Holtschmidt, H., and Schmelzer, H. G., French Pat. 1,379,156 (1964); Chem. Abstr.

    Google Scholar 

  101. Degener, E., and Holtschmidt, H., German Pat. 1,224,305 (1966)

    Google Scholar 

  102. Degener, E., and Holtschmidt, H., Chem. Abstr. 65, 20071 (1966).

    Google Scholar 

  103. Degener, E., Schmelzer, H. G., and Holtschmidt, H., Angew. Chem. Intern. Ed. 5, 960 (1966).

    Article  CAS  Google Scholar 

  104. Derkach, G. I., Zh. Obshch. Khim. 29, 241 (1959)

    CAS  Google Scholar 

  105. Derkach, G. I., Chem. Abstr. 53, 21750 (1959).

    Google Scholar 

  106. Derkach, G. I., Lepesa, A. M., and Kirsanov, A. V., Zh. Obshch. Khim. 31, 3424 (1961)

    CAS  Google Scholar 

  107. Derkach, G. I., Lepesa, A. M., and Kirsanov, A. V., Chem. Abstr. 57, 3353 (1962).

    Google Scholar 

  108. Derkach, G. I., Gubnitskaya, E. S., and Kirsanov, A. V., Zh. Obshch. Khim. 31, 3746 (1961)

    CAS  Google Scholar 

  109. Derkach, G. I., Gubnitskaya, E. S., and Kirsanov, A. V., Chem. Abstr. 57, 9735 (1962).

    Google Scholar 

  110. Derkach, G. I., Gubnitskaya, E. S., and Kirsanov, A. V., Zh. Obshch. Khim. 31, 3679 (1961)

    CAS  Google Scholar 

  111. Derkach, G. I., Gubnitskaya, E. S., and Kirsanov, A. V., Chem. Abstr. 57, 9876 (1962).

    Google Scholar 

  112. Derkach, G. I., and Rudavskii, V. P., Zh. Obshch. Khim. 35, 1202 (1965)

    CAS  Google Scholar 

  113. Derkach, G. I., and Rudavskii, V. P., Chem. Abstr. 63, 11398 (1965).

    Google Scholar 

  114. Dimroth, O., and Zoeppritz, F., Ber. 35, 995 (1902).

    Google Scholar 

  115. Dimroth, P., German Pat. 1,166,771 (1964).

    Google Scholar 

  116. Eilingsfeld, H., Seefelder, M., and Weidinger, H., Angew. Chem. 72, 836 (1960).

    Article  CAS  Google Scholar 

  117. Eilingsfeld, H., Seefelder, M., and Weidinger, H., German Pat. 1,119,872 (1960).

    Google Scholar 

  118. Eilingsfeld, H., Seefelder, M., and Weidinger, H., Ber. 96, 2671 (1963).

    CAS  Google Scholar 

  119. Eilingsfeld, H., Seefelder, M., and Weidinger, H., Ber. 96, 2899 (1963).

    CAS  Google Scholar 

  120. Eistert, B., and Häupter, F., Ber. 92, 1921 (1959).

    CAS  Google Scholar 

  121. Ermill, A., Castro, A. J., and Westfall, P. A., J. Org. Chem. 30, 339 (1965).

    Article  Google Scholar 

  122. Farbenfabriken Bayer, A.G., British Pat. 917,436 (1963)

    Google Scholar 

  123. Farbenfabriken Bayer, A.G., Chem. Abstr. 58, 12425 (1963).

    Google Scholar 

  124. Fawcett, F. S., Tullock, C. W., and Coffman, D. D., J. Am. Chem. Soc. 84, 22 (1962).

    Article  Google Scholar 

  125. Fawcett, F. S., Tullock, C. W., and Coffman, D. D., J. Am. Chem. Soc. 84, 4275 (1962).

    Article  CAS  Google Scholar 

  126. Fieser, L. F., and Hershberg, E. B., J. Am. Chem. Soc. 60, 2547 (1938).

    Google Scholar 

  127. Fieser, L. F., and Hartwell, J. L., J. Am. Chem. Soc. 60, 2555 (1938).

    Article  CAS  Google Scholar 

  128. Fieser, L. F., and Jones, J. E., J. Am. Chem. Soc. 64, 1666 (1945).

    Article  Google Scholar 

  129. Fieser, L. F., Hartwell, J. L., and Jones, J. E., in “Organic Synthesis Collective Volumes,” Vol. 3, J. Wiley and Sons, New York (1955), p. 98.

    Google Scholar 

  130. Finkbeiner, H., J. Org. Chem. 30, 2861 (1965).

    Article  CAS  Google Scholar 

  131. Fischer, O., Müller, A., and Vilsmeier, A., J. Prakt. Chem. [2] 198, 60 (1925).

    Google Scholar 

  132. Fischer, R., and Pasedach, H., German Pat. 1,133,717 (1962).

    Google Scholar 

  133. Friedel, M. C., Bull. Soc. Chim. [3] 61, 1027 (1894).

    Google Scholar 

  134. Godefroy, E. F., van der Eycken, C. A. M., and Janssen, P. A., J. Org. Chem. 32, 1259 (1967).

    Article  Google Scholar 

  135. Gold, H., Angew. Chem. 72, 956 (1960).

    Article  CAS  Google Scholar 

  136. Grdinic, M., and Hahn, V., J. Org. Chem. 30, 2381 (1965).

    Article  CAS  Google Scholar 

  137. Greenberg, B., and Aston, J. G., J. Org. Chem. 25, 1894 (1960).

    Article  CAS  Google Scholar 

  138. Grundmann, C., Weisse, G., and Seide, S., Ann. 577, 77 (1952).

    CAS  Google Scholar 

  139. Grundmann, C., and Dean, J. M., Angew. Chem. Intern. Ed. 4, 955 (1965).

    Article  Google Scholar 

  140. Hafner, K., and Bernhard, C., Angew. Chem. 64, 533 (1957).

    Article  Google Scholar 

  141. Hafner, K., and Vöpel, K. M., Angew. Chem. 71, 672 (1959).

    Article  CAS  Google Scholar 

  142. Hafner, K., Angew. Chem. 72, 574 (1960).

    Google Scholar 

  143. Hafner, K., Vöpel, K. H., Ploss, G., and König, C., Ann. 666, 52 (1963).

    Google Scholar 

  144. Hafner, K., German Pat. 1,105,411 (1961).

    Google Scholar 

  145. Hagedorn, I., and Tönges, H., Pharmazie 12, 570 (1957).

    Google Scholar 

  146. Hagedorn, I., Etling, H., and Lichtel, K. E., Ber. 99, 520 (1966).

    CAS  Google Scholar 

  147. Hahn, V., and Grdinic, M., Chem. Eng. Data 11, 211 (1966).

    Article  CAS  Google Scholar 

  148. Hall, H. K., Jr., J. Am. Chem. Soc. 77, 5993 (1955).

    Article  CAS  Google Scholar 

  149. Hall, H. K., Jr., J. Am. Chem. Soc. 78, 2717 (1956).

    Article  CAS  Google Scholar 

  150. Hallmann, F., Ber. 9, 846 (1876).

    Article  Google Scholar 

  151. Hansen, H. V., Caputo, J. A., and Meitzer, R. I., J. Org. Chem. 31, 3845 (1966).

    Article  CAS  Google Scholar 

  152. Hantzsch, A., Ber. 64, 667 (1931).

    Google Scholar 

  153. Held, P., German Pat. (East) 32,562 (1964)

    Google Scholar 

  154. Held, P., Chem. Abstr. 63, 13107 (1965).

    Google Scholar 

  155. Hertler, W. R., and Corey, E. J., J. Org. Chem. 23, 1221 (1958).

    Article  CAS  Google Scholar 

  156. Hettler, H., Tetrahedron Letters 4049 (1966).

    Google Scholar 

  157. Hickmott, P. W., J. Chem. Soc. 666 (1966).

    Google Scholar 

  158. Hilgetag, G., Zieloff, K., and Paul, H., Angew. Chem. 77, 261 (1965).

    Article  CAS  Google Scholar 

  159. Hinkel, L. E., and Treharne, G. J., J. Chem. Soc. 866 (1945).

    Google Scholar 

  160. Hoesch, K., Ber. 48, 1122 (1915).

    Article  CAS  Google Scholar 

  161. Holsten, J. R., and Lilyquist, M. R., United States Pat. 3,210,422 (1965)

    Google Scholar 

  162. Holsten, J. R., and Lilyquist, M. R., Chem. Abstr. 63, 17990 (1965).

    Google Scholar 

  163. Holtschmidt, H., Angew. Chem. Intern. Ed. 1, 632 (1962).

    Article  Google Scholar 

  164. Holtschnudt, H., Degener, E., and Schmelzer, H. G., Ann. 701, 107 (1967).

    Google Scholar 

  165. Hoechster Farbwerke, German Pat. 41,751; 44,077 (1887).

    Google Scholar 

  166. Holy, A., and Arnold, Z., Coll. Czech. Chem. Commun. 30, 53 (1964).

    Article  CAS  Google Scholar 

  167. Howard, Jr., E. G., United States Pat. 2,810,726 (1957).

    Google Scholar 

  168. Huisgen, R., Stangl, H., Sturm, H. J., and Wagenhofer, H., Angew. Chem. Intern. Ed. 1, 50 (1962).

    Article  Google Scholar 

  169. Huisgen, R., and Raab, R., Tetrahedron Letters 649 (1966).

    Article  Google Scholar 

  170. Ichimura, K., and Ohta, M., Tetrahedron Letters 807 (1966).

    Article  Google Scholar 

  171. Ishikawa, S., Sci. Papers Inst. Phys. Chem. Res. Tokyo 7, 293 (1927).

    Google Scholar 

  172. Ito, Y., Katsuragawa, S., Okano, M., and Oda, R., Tetrahedron letters 1321 (1965).

    Article  Google Scholar 

  173. Ito, Y., Okano, M., and Oda, R., Tetrahedron 22, 447 (1966).

    Article  CAS  Google Scholar 

  174. Ito, Y., Katsuragawa, S., Okano, M., and Oda, R., Tetrahedron 23, 2159 (1967).

    Article  CAS  Google Scholar 

  175. Janz, G. J., and Danyluk, S. S., J. Am. Chem. Soc. 81, 3846 (1959).

    Article  CAS  Google Scholar 

  176. Janz, G. J., and Danyluk, S. S., J. Am. Chem. Soc. 81, 3850 (1959).

    Article  CAS  Google Scholar 

  177. Janz, G. J., and Danyluk, S. S., J. Am. Chem. Soc. 81, 3854 (1959).

    Article  CAS  Google Scholar 

  178. Jentzsch, W., Ber. 97, 1361 (1964).

    CAS  Google Scholar 

  179. Jentzsch, W., and Seefelder, M., German Pat. 1,172,269 (1964).

    Google Scholar 

  180. Jentzsch, W., and Seefelder, M., German Pat. 1,175,223 (1964).

    Google Scholar 

  181. Jentzsch, W., Ber. 97, 2755 (1964).

    CAS  Google Scholar 

  182. Jentzsch, W., and Seefelder, M., Ber. 98, 274 (1965).

    CAS  Google Scholar 

  183. Johnson, F., and Nasutavicus, W. A., J. Heterocyclic Chem. 2, 26 (1965).

    Article  CAS  Google Scholar 

  184. Johnson, F., and Madronero, R., Advances in Heterocyclic Chemistry, Vol. 6, Academic Press, New York (1966), p. 131.

    Google Scholar 

  185. Jostes, F., German Pat. 547,108 (1929).

    Google Scholar 

  186. Jutz, C., Ser. 91, 850 (1958).

    CAS  Google Scholar 

  187. Jutz, C., Ser. 97, 2050 (1964).

    CAS  Google Scholar 

  188. Jutz, C., Müller, E., Ber. 99, 2479 (1966).

    CAS  Google Scholar 

  189. Jutz, C., and Müller, W., Angew. Chem. Intern. Ed. 5, 1042 (1966).

    Article  CAS  Google Scholar 

  190. Jutz, C., and Müller, W., Ber. 100, 1536 (1967).

    CAS  Google Scholar 

  191. Kalischer, G., Scheyer, H., and Keller, K., German Pat. 514,415; 519,444; 519,806 (1927).

    Google Scholar 

  192. King, W. J., and Nord, F. F., J. Org. Chem. 13, 635 (1948).

    Article  PubMed  CAS  Google Scholar 

  193. King, W. J., and Nord, F. F., J. Org. Chem. 14, 405 (1949).

    Article  CAS  Google Scholar 

  194. Kirsanov, A. V., Izv. Akad. Nauk SSSR, Otd. Khim. Nauk, 646 (1954)

    Google Scholar 

  195. Kirsanov, A. V., Chem. Abstr. 49, 13161 (1955).

    Google Scholar 

  196. Kirsanov, A. V., and Derkach, G. I., Zh. Obshch. Khim. 26, 2009 (1956)

    CAS  Google Scholar 

  197. Kirsanov, A. V., and Derkach, G. I., Chem. Abstr. 51, 1821 (1957).

    Google Scholar 

  198. Kirsanov, A. V., and Derkach, G. I., Zh. Obshch. Khim. 27, 3248 (1957)

    CAS  Google Scholar 

  199. Kirsanov, A. V., and Derkach, G. I., Chem. Abstr. 52, 8997 (1958).

    Google Scholar 

  200. Kirsanov, A. K., and Derkach, G. I., Zh. Obshch. Khim. 28, 1187 (1958)

    Google Scholar 

  201. Kirsanov, A. V., and Derkach, G. I., Chem. Abstr. 53, 1208 (1959).

    Google Scholar 

  202. Kirsanov, A. V., Bodnarchuk, M. D., and Shevchenko, V. I., Dopovidi Akad. Nauk Ukr. RSR, 221, (1963)

    Google Scholar 

  203. Kirsanov, A. V., Bodnarchuk, M. D., and Shevchenko, V. I., Chem. Abstr. 59, 12666 (1963).

    Google Scholar 

  204. Klages, F., and Grill, W., Ann. 594, 21 (1955).

    Google Scholar 

  205. Klutchko, S., Hansen, H. K., and Melzer, R. I., J. Org. Chem. 30, 3454 (1965).

    Article  CAS  Google Scholar 

  206. Koike, E., Obayashi, K., Oka, R., Taura, S., and Takada, H., Japanese Pat. 19,100 (1965)

    Google Scholar 

  207. Koike, E., Obayashi, K., Oka, R., Taura, S., and Takada, H., Chem. Abstr. 63, 16263 (1965).

    Google Scholar 

  208. Kotjscheff, T., Wolf, F., and Wolter, G., Z.Chem. 6, 148 (1966)

    Google Scholar 

  209. Kotjscheff, T., Wolf, F., and Wolter, G., Chem. Abstr. 65, 7051 (1966).

    Google Scholar 

  210. Kreutzkamp, N., and Cordes, G., Ann. 623, 103 (1959).

    CAS  Google Scholar 

  211. Krieble, V. K., and Peiker, A. L., J. Am. Chem. Soc. 51, 3368 (1929).

    Article  CAS  Google Scholar 

  212. Kühle, E., Angew. Chem. Intern. Ed. 1, 647 (1962).

    Article  Google Scholar 

  213. Kühle, E., Belgian Pat. 660,171 (1965)

    Google Scholar 

  214. Kühle, E., Chem. Abstr. 64, 603 (1966).

    Google Scholar 

  215. Lander, G. C., and Laws, H. E., J. Chem. Soc. 85, 1695 (1904).

    Article  CAS  Google Scholar 

  216. Leo H., Ber. 10, 2133 (1877).

    Article  Google Scholar 

  217. Leuchs, H., Wulkow, G., and Gerland, H., Ber. 65, 1586 (1932).

    Google Scholar 

  218. Leuchs, H., and Schlötzer, A., Ber. 67, 1572 (1934).

    Google Scholar 

  219. Levy, P. R., and Stephen, H., J. Chem. Soc. 985 (1956).

    Google Scholar 

  220. Ley, H., Ber.31,240 (1898).

    Article  CAS  Google Scholar 

  221. Ley, H., and Holzweissig, E., Ber. 36, 18 (1903).

    Article  CAS  Google Scholar 

  222. Lorenz, H., and Wizinger, R., Helv. Chim. Acta 28, 6000 (1945).

    Article  Google Scholar 

  223. Ludsteck, D., Neubauer, G., Pasedach, H., and Seefelder, M., German Pat. 1,133,716 (1962).

    Google Scholar 

  224. McDonald, R. N., and Krueger, R. A., J. Org. Chem. 28, 2542 (1963).

    Article  CAS  Google Scholar 

  225. Martin, D., and Weise, A., Ann. 702, 86 (1967).

    CAS  Google Scholar 

  226. Martin, G., and Martin, M., Bull. Soc. Chim. France 637 (1963)

    Google Scholar 

  227. Martin, G., and Martin, M., Chem. Abstr. 60, 391 (1964).

    Google Scholar 

  228. Mazalov, S. A., and Sokolov, S. V., Zh. Obshch. Khim. 36, 1330 (1966)

    CAS  Google Scholar 

  229. Mazalov, S. A., and Sokolov, S. V., Chem. Abstr. 65, 16851 (1966).

    Google Scholar 

  230. Meerwein, H., Laasch, P., Mersch, R., and Spille, J., Ber. 89, 209 (1956).

    CAS  Google Scholar 

  231. Michael, A., and Wing, J. F., Am. Chem. J. 7, 71 (1885).

    Article  Google Scholar 

  232. Mitin, Y. V., and Vlasov, G. P., Probl. Organ. Sinteza, Akad. Nauk SSSR, 297 (1965)

    Google Scholar 

  233. Mitin, Y. V., and Vlasov, G. P., Chem. Abstr. 64, 11122 (1966).

    Google Scholar 

  234. Mory, R., Stöcklin, E., and Schmid, M., German Pat. 1,026,750 (1958)

    Google Scholar 

  235. Mory, R., Stöcklin, E., and Schmid, M., Chem. Abstr. 55, 5428 (1961).

    Google Scholar 

  236. Mumm, O., Ber. 43, 886 (1910).

    Article  CAS  Google Scholar 

  237. Mumm, O., and Hesse, H., Ber. 43, 2508 (1910).

    Google Scholar 

  238. Murakami, M., Akagi, K., and Takahashi, K., J. Am. Chem. Soc. 83, 2002 (1961).

    Article  CAS  Google Scholar 

  239. Namanworth, E., Dissertation, Yale University, 1965.

    Google Scholar 

  240. Nef, J. U., Ann. 270, 267 (1892).

    Google Scholar 

  241. Nef, J. U., Ann. 280, 298 (1894).

    Google Scholar 

  242. Nef, J.U., Ann 287, 301 (1895).

    Google Scholar 

  243. Neidlein, R., and Bottler, R., Tetrahedron Letters 1069 (1966).

    Article  Google Scholar 

  244. Nenitzescu, C. D., and Isacescu, D., Bull. Soc. Chim. (Rumania) 11, 135 (1929).

    Google Scholar 

  245. Oda, R., Katsuragawa, S., Ito, Y., and Okano, M., Nippon Kagaku Zasshi 87, 1236 (1966).

    Article  CAS  Google Scholar 

  246. Oda, R., Katsuragawa, S., Ito, Y., and Okano, M., Nippon Kagaku Zasshi 87,490 (1966).

    Article  CAS  Google Scholar 

  247. Okawa, K., Abe, J., Watanabe, T., and Fujimoto, K., Japanese Pat. 13,726 (1965)

    Google Scholar 

  248. Okawa, K., Abe, J., Watanabe, T., and Fujimoto, K., Chem. Abstr. 63, 14774 (1965).

    Google Scholar 

  249. Paquette, L. A., Johnson, B. A., and Hinga, F. M., Org. Syn. 46, 118 (1966).

    Google Scholar 

  250. Parham, W. E., Roder, T. M., and Hasek, W. R., J. Am. Chem. Soc. 75, 1647 (1953).

    Article  CAS  Google Scholar 

  251. Paul, H., Weise, A., and Dettmer, R., Ber. 98, 1450 (1965).

    CAS  Google Scholar 

  252. Pechmann, H. v., Ber. 33, 611 (1900).

    Article  Google Scholar 

  253. Peterson, S. W., and Williams, J. M., J. Am. Chem. Soc. 88, 2866 (1966).

    Article  CAS  Google Scholar 

  254. Porai-Koshits, B. A., Kvitko, I. Y., and Favorskii, O. V., Zh. Organ. Khim. 1, 1516 (1965)

    CAS  Google Scholar 

  255. Porai-Koshits, B. A., Kvitko, I. Y., and Favorskii, O. V., Chem. Abstr. 64, 698 (1966).

    Google Scholar 

  256. Porai-Koshits, B. A., Kvitko, I. Y., and Shutkova, E. A., Latvijas PSR Zinatnu Akad. Vestis, Khim. Ser. 587 (1965)

    Google Scholar 

  257. Porai-Koshits, B. A., Kvitko, I. Y., and Shutkova, E. A., Chem. Abstr. 64, 8168 (1966).

    Google Scholar 

  258. Prajsnar, B., Zeszyty Nauk Politech. Slask. Chem. No. 20 (1963)

    Google Scholar 

  259. Prajsnar, B., Chem. Abstr. 62, 16019 (1965).

    Google Scholar 

  260. Prajsnar, B., Zeszyty Nauk Politech. Slask. Chem. No. 24, 241 (1964)

    Google Scholar 

  261. Prajsnar, B., Chem. Abstr. 63, 11289 (1965).

    Google Scholar 

  262. Quang, Y. V., Cadiot, P., Willemart, A., Compt. Rend. 248, 2356 (1959).

    CAS  Google Scholar 

  263. Rätz, R., and Sweeting, O. J., J. Org. Chem. 28, 1608 (1963).

    Article  Google Scholar 

  264. Rätz, R., and Sweeting, O. J., J. Org. Chem. 30, 438 (1965).

    Article  Google Scholar 

  265. Ricci, A., Balucani, D., and Buu-Hoi, N. P., J. Chem. Soc. 779 (1967).

    Google Scholar 

  266. Ried, W., and Junker, P., Ann. 700, 32 (1966).

    CAS  Google Scholar 

  267. Roh, N., German Pat. 645,880 (1935); 660, 693 (1935).

    Google Scholar 

  268. Roh, N., and Kochendörfer, G., German Pat. 677,207 (1937).

    Google Scholar 

  269. Rogers, M. A. T., Chem. Soc. 596 (1943).

    Google Scholar 

  270. Sayigh, A. A. R., and Ulrich, H., J. Chem. Soc. 3146 (1963).

    Google Scholar 

  271. Schand, E. W., United States Pat. 2,411,064 (1946)

    Google Scholar 

  272. Schand, E. W., Chem. Abstr. 41, 1236 (1947).

    Google Scholar 

  273. Schicke, H. G., Belgian Pat. 664,091 (1965)

    Google Scholar 

  274. Schicke, H. G, Chem. Abstr. 65, 659 (1966).

    Google Scholar 

  275. Schmelzer, H. G., Degener, E., and Holtschmidt, A., Angew. Chem. Intern. Ed. 5, 960 (1966).

    Article  CAS  Google Scholar 

  276. Schroeter, G., Ber. 42, 3360 (1909).

    Google Scholar 

  277. Schulte, K. E., Reisch, J., and Stoess, U., Angew. Chem. Intern. Ed. 4, 1081 (1965).

    Article  CAS  Google Scholar 

  278. Seefelder, M., German Pat. 1,167,819 (1964)

    Google Scholar 

  279. Seefelder, M., Chem. Abstr. 61, 1761 (1964).

    Google Scholar 

  280. Seefelder, M., German Pat. 1,204,663 (1965)

    Google Scholar 

  281. Seefelder, M., Chem. Abstr. 64, 2025 (1966).

    Google Scholar 

  282. Seus, E. J., J. Org. Chem. 30, 2818 (1965).

    Article  CAS  Google Scholar 

  283. Shabica, A. C., Howe, E. E., Ziegler, J. B., and Tishler, M., J. Am. Chem. Soc. 68, 1156 (1946).

    Article  CAS  Google Scholar 

  284. Shevchenko, V. I., Bodnarchuk, N. D., and Kirsanov, A. V., Zh. Obshch. Khim. 33, 1342 (1963)

    CAS  Google Scholar 

  285. Shevchenko, V. I., Bodnarchuk, N. D., and Kirsanov, A. V., Chem. Abstr. 59, 11239 (1963).

    Google Scholar 

  286. Shevchenko, V. I., and Kukhar, V. P., Zh. Obshch. Khim. 36, 1260 (1966)

    Google Scholar 

  287. Shevchenko, V. I., and Kukhar, V. P., Chem. Abstr. 65, 16845 (1966).

    Google Scholar 

  288. Silverstein, R. M., Ryskiewicz, E. E., Willard, C., and Koehler, C., J. Org. Chem. 20, 668 (1955).

    Article  CAS  Google Scholar 

  289. Simchen, G., Angew. Chem. Intern. Ed. 5, 663 (1966).

    Article  CAS  Google Scholar 

  290. Smissman, E. E., and Diebold, J. L., J. Org. Chem. 30, 4002 (1965).

    Article  CAS  Google Scholar 

  291. Smith, G.F., J.Chem. Soc. 3842 (1954).

    Google Scholar 

  292. Smith, T. D., J. Chem. Soc. A, 841 (1966).

    Article  Google Scholar 

  293. Sommers, A. H., Michaels, R. J., Jr., and Weston, A. W., J. Am. Chem. Soc. 74, 5546 (1951).

    Article  Google Scholar 

  294. Sonn, A., and Müller, E., Ber. 52, 1927 (1919).

    Google Scholar 

  295. Spaenig, H., and Schoenleben, W., Belgian Pat. 635,435 (1964)

    Google Scholar 

  296. Spaenig, H., and Schoenleben, W., Chem. Abstr. 61, 13334 (1964).

    Google Scholar 

  297. Speziale, A. J., and Freeman, R. C., J. Am. Chem. Soc. 82, 903 (1960).

    Article  CAS  Google Scholar 

  298. Speziale, A. J., and Smith, L. R., J. Org. Chem. 27, 4361 (1962).

    Article  CAS  Google Scholar 

  299. Speziale, A. J., and Smith, L. R., J. Org. Chem. 28, 3492 (1963).

    Article  CAS  Google Scholar 

  300. Speziale, A. J., Smith, L. R., and Fedder, J. R., J. Org. Chem. 30, 4303 (1965).

    Article  CAS  Google Scholar 

  301. Speziale, A. J., and Smith, L. R., United States Pat. 3,230,255 (1966)

    Google Scholar 

  302. Speziale, A. J., and Smith, L. R., Chem. Abstr. 64, 8044 (1966).

    Google Scholar 

  303. Stamicorn, N. V., British Pat. 1,007,413 (1965)

    Google Scholar 

  304. Stamicorn, N. V., Chem. Abstr. 64, 8158 (1966).

    Google Scholar 

  305. Stepanov, B. I., and Migachev, G. L, Zh. Vses. Khim. Obshchestva im. D.I. Mendeleeva 11, 472 (1966).

    CAS  Google Scholar 

  306. Stephen, H. J., J. Chem. Soc. 117, 1529 (1920).

    Article  CAS  Google Scholar 

  307. Stephen, H., and Staskun, B., J. Chem. Soc. 980 (1956).

    Google Scholar 

  308. Stevens, C. L., and French, J. C., Am. Chem. Soc. 75, 657 (1953).

    Article  CAS  Google Scholar 

  309. Stevens, C. L., and French, J. C., J. Am. Chem. Soc. 76, 4398 (1954).

    Article  Google Scholar 

  310. Stevens, T. E., J. Org. Chem. 32, 670 (1967).

    Article  CAS  Google Scholar 

  311. Stewart, R., and Clark, R. H., J. Am. Chem. Soc. 69, 713 (1949).

    Article  Google Scholar 

  312. Tafel, J., and Wassmuth, O., Ber. 40, 2841 (1907).

    Google Scholar 

  313. Thurman, J. C., Chem. Ind. (London) 752 (1964).

    Google Scholar 

  314. Treibs, W., Hiebsch, A., and Neupert, H. V., Naturwiss. 44, 352 (1957).

    Article  Google Scholar 

  315. Tullock, C. W., Coffman, D. D., and Mutterties, E. L., J. Am. Chem. Soc. 86, 357 (1964).

    Article  CAS  Google Scholar 

  316. Ugi, L, and Meyr, R., Angew. Chem. 70, 702 (1958).

    Article  CAS  Google Scholar 

  317. Ugi, I., and Meyr, R., Ber. 93, 239 (1960).

    CAS  Google Scholar 

  318. Ugi, I., Betz, W., Fetzer, U., and Offermann, K., Ber. 94, 2814 (1961).

    CAS  Google Scholar 

  319. Ugi, I., Beck, F., and Fetzer, U., Ber. 95, 126 (1962).

    CAS  Google Scholar 

  320. Ulrich, H., Tilley, J. N., and Sayigh, A. A. R., J. Org. Chem. 29, 2401 (1965).

    Article  Google Scholar 

  321. Ulrich, H., Tucker, B., and Sayigh, A. A. R., J. Org. Chem. 30, 2779 (1965).

    Article  CAS  Google Scholar 

  322. Ulrich, H., Tucker, B., and Sayigh, A. A. R., Angew. Chem. Intern. Ed. 6, 636 (1967).

    Article  CAS  Google Scholar 

  323. Ulrich, H., Tucker, B., and Sayigh, A. A. R., J. Org. Chem. 32, 4052 (1967).

    Article  CAS  Google Scholar 

  324. Ulrich, H., Tucker, B., and Sayigh, A. A. R., unpublished results.

    Google Scholar 

  325. Vilsmeier, A., and Haack, A., Ber. 60, 119 (1927).

    Google Scholar 

  326. Vilsmeier, A., Chemiker Z. 75, 133 (1951).

    Google Scholar 

  327. Vollmann, H., Becker, H., Corell, M., Streeck, H., and Langbein, G., Ann. 531, 1 (1937).

    CAS  Google Scholar 

  328. Wallach, O., Ber. 9, 1212 (1876).

    Article  Google Scholar 

  329. Wallach, O., and Hoffmann, M., Ann. 184, 75 (1877).

    Google Scholar 

  330. Wallach, O., Ann. 184, 1 (1877).

    Google Scholar 

  331. Wallach, O., Ann. 214, 193, 226 (1882).

    Google Scholar 

  332. Wallach, O., and Kamensky, H., Ann. 214, 234 (1882).

    Google Scholar 

  333. Walter, W., and Bode, K. D., Angew. Chem. Intern. Ed. 2, 510 (1962).

    Article  Google Scholar 

  334. Warren, W. H., and Wilson, F. E., Ber. 68, 957 (1935).

    Google Scholar 

  335. Weidinger, H., and Wellenreuther, G., British Pat. 927,974 (1963)

    Google Scholar 

  336. Weidinger, H., and Wellenreuther, G., Chem. Abstr. 60, 2987 (1964).

    Google Scholar 

  337. Weidinger, H., and Eilingsfeld, H., Belgian Pat. 631,291 (1963)

    Google Scholar 

  338. Weidinger, H., and Eilingsfeld, H., Chem. Abstr. 61, 4277 (1964).

    Google Scholar 

  339. Weidinger, H., and Eilingsfeld, H., German Pat. 1,192,180 (1965)

    Google Scholar 

  340. Weidinger, H., and Eilingsfeld, H., Chem. Abstr. 63, 6922 (1965).

    Google Scholar 

  341. Weidinger, H., and Kranz, J., Ber. 96, 2070 (1963).

    CAS  Google Scholar 

  342. Weise, W., Scheurer, G., Aumann, A., and Pommer, H., German Pat. 1,104,949 (1961).

    Google Scholar 

  343. Weissenfeis, M., Schurig, H., and Huehsam, G., Z. Chem. 6, 471 (1966)

    Article  Google Scholar 

  344. Weissenfeis, M., Schurig, H., and Huehsam, G., Chem. Abstr. 66, 55177f (1967).

    Google Scholar 

  345. Weston, A. W., and Michaels, I. R., Jr., J. Am. Chem. Soc. 72, 1422 (1950).

    Article  CAS  Google Scholar 

  346. Weston, A. W., and Michaels, I. R., Jr., Org. Syn. 31, 108 (1951).

    Article  CAS  Google Scholar 

  347. Wilson, C. D., United States Pat. 2,437,370 (1945).

    Google Scholar 

  348. Wilson, C. D., United States Pat. 2,558,285 (1947).

    Google Scholar 

  349. Wolf, W., Degener, E., and Petersen, S., Angew. Chem. 72, 963 (1960).

    Article  CAS  Google Scholar 

  350. Wolff, P., German Pat. 614,325; 615,130 (1933).

    Google Scholar 

  351. Wood, J. H., and Bost, R. W., J. Am. Chem. Soc. 59, 1722 (1937).

    Google Scholar 

  352. Yaroslavsky, S., Tetrahedron Letters 1503 (1965).

    Google Scholar 

  353. Zaoral, M., and Arnold, Z., Tetrahedron Letters 9 (1960).

    Google Scholar 

  354. Ziegenbein, W., and Franke, W., Angew. Chem. 71, 573 (1959).

    Article  CAS  Google Scholar 

  355. Ziegenbein, W., and Hornung, K. H., Ber. 93, 2976 (1962).

    Google Scholar 

  356. Ziegenbein, W., Lang, W., and Schmitt, J., German Pat. 1,125,902 (1962).

    Google Scholar 

  357. Ziegenbein, W., German Pat. 1,213,830 (1966)

    Google Scholar 

  358. Ziegenbein, W., Chem. Abstr. 64, 19497 (1966).

    Google Scholar 

  359. Ziegenbein, W., Angew. Chem. Intern. Ed. 4, 358 (1965).

    Article  Google Scholar 

  360. Zieloff, K., Paul, H., and Hilgetag, G., Ber. 99, 357 (1966).

    CAS  Google Scholar 

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Ulrich, H. (1968). Imidoyl Halides. In: The Chemistry of Imidoyl Halides. Springer, New York, NY. https://doi.org/10.1007/978-1-4684-8947-7_3

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