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Hydrazidoyl Halides

  • Henri Ulrich

Abstract

The chlorides derived from the reaction of aroyl phenylhydrazines with phosphorus pentachloride are recorded in the Hterature under a variety of names. While Chemical Abstracts lists these compounds as the phenylhydrazones of the corresponding acid chlorides (for example, benzoyl chloride phenylhydrazone for C6H5C(Cl)=NNHC6H5), Beilstein uses the terms α-chlorobenzyliden Phenylhydrazine or α-chlorobenzal phenylhydrazine for this compound. In view of the relationship of the chlorides I with the corresponding acid hydrazides (II), their hydrolysis products, the names hydrazide chlorides or hydrazidoyl chlorides are more appropriate. In order to preserve conformity of nomenclature, the latter name is used in this book.

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References

  1. 1.
    Bamish, I. T., and Gibson, M. S., Chem & Ind. (London) 1699 (1965).Google Scholar
  2. 2.
    Bamish, L T., and Gibson, M. S., J. Chem. Soc. 2999 (1965).Google Scholar
  3. 3.
    Bamish, I. T., and Gibson, M. S., Chem. Commun. 1001 (1967).Google Scholar
  4. 4.
    Bianchetti, G., Pocar, D., Dalla Croce, P., and Vigevani, A., Ber. 98, 2715 (1965).Google Scholar
  5. 5.
    Bowack, D. A., and Lapworth, A., J. Chem. Soc. 87, 1854 (1905).CrossRefGoogle Scholar
  6. 6.
    Bülow, C., and Neber, P. W., Ber. 45, 3732 (1912).CrossRefGoogle Scholar
  7. 7.
    Bülow, C., and Neber, P. W., Ber. 46, 2032, 2370 (1913).CrossRefGoogle Scholar
  8. 8.
    Bülow, C., and Neber, P. W., Ber. 46, 2370 (1913).CrossRefGoogle Scholar
  9. 9.
    Bülow, C., and Neber, P. W., Ber. 49, 2179 (1916).CrossRefGoogle Scholar
  10. 10.
    Bülow, C., and Huss, R., Ber. 50, 1480 (1917).CrossRefGoogle Scholar
  11. 11.
    Bülow, C., and Huss, R., Ber. 51, 28 (1918).Google Scholar
  12. 12.
    Bülow, C., Ber 51, 399 (1918).CrossRefGoogle Scholar
  13. 13.
    Bülow, C., and Engler, R., Ber. 51, 1264 (1918).Google Scholar
  14. 14.
    Bülow, C., and Engler, R., Ber. 52, 632 (1919).Google Scholar
  15. 15.
    Bülow, C., and Seidel, F., Ber. 57, 629 (1924).Google Scholar
  16. 16.
    Bülow, C., and King, E., Ann. 439, 216 (1924).Google Scholar
  17. 17.
    Bülow, C., and Spengler, W., Ber. 58, 1375 (1925).Google Scholar
  18. 18.
    Burgess, J. M., and Gibson, M. S., Tetrahedron 18, 1001 (1962).CrossRefGoogle Scholar
  19. 19.
    Burgess, J. M., and Gibson, M. S., J. Chem. Soc. 1500 (1964).Google Scholar
  20. 20.
    Chattaway, F. D., and Walker, A. J., J. Chem. Soc. 975 (1925).Google Scholar
  21. 21.
    Chattaway, F. D., and Walker, A. J., Chem. Soc. 1687 (1925).Google Scholar
  22. 22.
    Chattaway, F. D., and Walker, A. J., J. Chem. Soc. 2407 (1925).Google Scholar
  23. 23.
    Chattaway, F. D., and Walker, A. J., J. Chem. Soc. 323 (1927).CrossRefGoogle Scholar
  24. 24.
    Chattaway, F. D., and Daldy, F. G., J. Chem. Soc. 2760 (1928).Google Scholar
  25. 25.
    Chattaway, F. D., and Irving, H., J. Chem. Soc. 91 (1930).Google Scholar
  26. 26.
    Chattaway, F. D., and Farinholt, L. H., J. Chem. Soc. 95 (1930).Google Scholar
  27. 27.
    Chattaway, F, D., and Adamson, A. B., J. Chem. Soc. 158 (1930).Google Scholar
  28. 28.
    Chattaway, F. D., and Adamson, A. B., J. Chem. Soc. 843 (1930).Google Scholar
  29. 29.
    Chattaway, F. D., and Irving, H., J. Am. Chem. Soc. 54, 263 (1932).CrossRefGoogle Scholar
  30. 30.
    Chattaway, F. D., and Lye, R. J., Proc. Roy. Soc. 135, 286 (1932).CrossRefGoogle Scholar
  31. 31.
    Chattaway, F. D., and Lye, R. J., J. Chem. Soc. 480 (1933).Google Scholar
  32. 32.
    Chattaway, F. D., and Ashworth, D. R., J. Chem. Soc. 1390, 1393 (1933).Google Scholar
  33. 33.
    Chattaway, F. D., and Parkers, G. D., J. Chem. Soc. 1007 (1935).Google Scholar
  34. 34.
    Ciusa, R., and Mega, P., Gazz. Chim. Ital 58, 836 (1928).Google Scholar
  35. 35.
    Clovis, J. S., Eckell, A., Huisgen, R., Wallbillich, G., and Webemdoerfer, B., Ber. 100, 1593(1967).Google Scholar
  36. 36.
    Dieckmann, W., and Platz, L., Ber. 38, 2987 (1905).Google Scholar
  37. 37.
    Dubenko, R. G., and Pel’kis, P. S., Zh. Obshch. Khim. 33, 3917 (1963).Google Scholar
  38. 38.
    Dubenko, R. G., and Pel’kis, P. S., Zh. Obshch. Khim. 34, 679 (1964).Google Scholar
  39. 39.
    Dubenko, R. G., and Pel’kis, P. S., Zh. Obshch Khim. 34, 3481 (1964).Google Scholar
  40. 40.
    Evdokimov, U., Gazz. Chim. Ital. 87, 1191 (1957).Google Scholar
  41. 41.
    Favrel, G., Compt. Rend. 134, 1312 (1902).Google Scholar
  42. 42.
    Favrel, G., Bull. Soc. Chim. France [4] 41, 1494 (1927).Google Scholar
  43. 43.
    Favrel, G., and Chrz, J., Bull. Soc. Chim. France [4] 41, 1603 (1927).Google Scholar
  44. 44.
    Fusco, R., and Justoni, R., Gazz. Chim. Ital. 67, 3 (1937).Google Scholar
  45. 45.
    Fusco, R., and Musante, C., Gazz. Chim. Ital. 68, 147, 154 (1938).Google Scholar
  46. 46.
    Fusco, R., and Musante, C., Gazz. Chim. Ital. 68, 665, 675, 677 (1938).Google Scholar
  47. 47.
    Fusco, R., Gazz. Chim. Ital. 69, 344, 348, 353, 359 (1939).Google Scholar
  48. 48.
    Fusco, R., and Pizzotti, R., Gazz. Chim. Ital. 72, 411 (1942).Google Scholar
  49. 49.
    Fusco, R., and Romani, R., Gazz. Chim. Ital. 78, 342 (1948).Google Scholar
  50. 50.
    Fusco, R., and Rossi, S., Gazz. Chim. Ital 86, 491 (1956).Google Scholar
  51. 51.
    Fusco, R., and Bianchetti, G., Gazz. Chim. Ital. 87, 441 (1957).Google Scholar
  52. 52.
    Fusco, R., Bianchetti, G., and Pocar, D., Gazz. Chim. Ital. 91, 1233 (1961).Google Scholar
  53. 53.
    Gaudiano, G., Umani-Ronchi, A., Bravo, P., and Acampora, M., Tetrahedron Letters 107(1967).Google Scholar
  54. 54.
    Gibson, M. S., J. Chem. Soc. 2270 (1962).CrossRefGoogle Scholar
  55. 55.
    Gibson, M. S., Tetrahedron 18, 1377 (1962).CrossRefGoogle Scholar
  56. 56.
    Gibson, M. S., Tetrahedron 19, 1587 (1963).CrossRefGoogle Scholar
  57. 57.
    Grünanger, P., and Langella, M. R., Gazz. Chim. Ital. 90, 229, 234 (1960).Google Scholar
  58. 58.
    Hegarty, A. F., and Scott, F. L., Tetrahedron Letters 3801 (1965).Google Scholar
  59. 59.
    Huisgen, R., and Koch, H. J., Ann. 591, 218, 226 (1955).Google Scholar
  60. 60.
    Huisgen, R., Seidel, M., Sauer, J., McFarland, J. W., and Wallbillich, G., J. Org. Chem. 24, 892 (1959).CrossRefGoogle Scholar
  61. 61.
    Huisgen, R., Sauer, J., Sturm, H. J., and Markgraf, J. H., Ber. 93, 2106 (1960).Google Scholar
  62. 62.
    Huisgen, R., Sauer, J., and Seidel, M., Ber. 93, 2885 (1960).Google Scholar
  63. 63.
    Huisgen, R., Strum, H. J., and Seidel, M., Ber. 94, 1555 (1961).Google Scholar
  64. 64.
    Huisgen, R., Seidel, M., Wallbillich, G., and Knupfer, H., Tetrahedron 17, 3, 18 (1962).Google Scholar
  65. 65.
    Huisgen, R., Grashey, R., Seidel, M., Knupfer, H., and Schmidt, R., Ann. 685, 169 (1962).Google Scholar
  66. 66.
    Huisgen, R., Angew. Chem. Intern. Ed. 2, 565 (1963).CrossRefGoogle Scholar
  67. 66a.
    Huisgen, R., Grashey, R., Knupfer, H., Kunz, R., and Seidel, M., Ber. 97, 1085 (1964).Google Scholar
  68. 67.
    Huisgen, R., Grashey, R., Aufderhaar, E., and Kunz, R., Ber. 98, 642 (1965).Google Scholar
  69. 68.
    Huisgen, R., Aufderhaar, E., and Wallbillich, G., Ber. 98, 1476 (1965).Google Scholar
  70. 69.
    Huisgen, R., and Webemdörder, V., Ber. 100, 71 (1967).Google Scholar
  71. 70.
    Huisgen, R., Sustmann, R., and Wallbillich, G., Ber. 100, 1786 (1967).Google Scholar
  72. 71.
    Humphries, J. E., Bloom, E., and Evans, R., J. Chem. Soc. 123, 1766 (1923).CrossRefGoogle Scholar
  73. 72.
    Humphries, J. E., Humble, H., and Evans, R., J. Chem. Soc. 1304 (1925).Google Scholar
  74. 73.
    Issleib, K., and Balszuweit, A., Ber. 99, 1316 (1966).Google Scholar
  75. 74.
    Justoni, R., Gazz. Chim. Ital. 68, 49 (1938).Google Scholar
  76. 75.
    Justoni, R., and Fusco, R., Gazz. Chim. Ital. 68, 59 (1938).Google Scholar
  77. 76.
    Krollpfeiffer, F., and Hartmann, H., Ber. 83, 90, 92 (1950).Google Scholar
  78. 77.
    Lozinskii, M. O., and Pel’kis, P. S., Zh. Obshch. Khim. 31, 1621 (1961).Google Scholar
  79. 78.
    Lozinskii, M. O., and Pel’kis, P. S., Zh. Obshch. Khim. 32, 526 (1962).Google Scholar
  80. 79.
    Lozinskii, M. O., Pel’kis, P. S., and Sanova, S. N., Zh. Obshch. Khim. 33, 2231 (1963).Google Scholar
  81. 80.
    Lozinskii, M. O., Ukrain. Chem. J. 30, 68 (1964).Google Scholar
  82. 81.
    Lozinskii, M. O., and Pel’kis, P. S., Zh. Organ. Khim. 1, 1415 (1965)Google Scholar
  83. Lozinskii, M. O., and Pel’kis, P. S., Chem. Abstr. 64, 621 (1966).Google Scholar
  84. 82.
    Lozinskii, M. O., and Pel’kis, P. S., Zh. Organ. Khim. 1, 1793 (1965)Google Scholar
  85. Lozinskii, M. O., and Pel’kis, P. S., Chem. Abstr. 64, 5063 (1966).Google Scholar
  86. 83.
    Lozinskii, M. O., Pel’kis, P. S., and Sanova, S. N., Zh. Organ. Khim. 1, 1800 (1965)Google Scholar
  87. Lozinskii, M. O., Pel’kis, P. S., and Sanova, S. N., Chem. Abstr. 64, 4974 (1966).Google Scholar
  88. 84.
    Lozinskii, M. O., Lopatinskaya, N. A., and Pel’kis, P. S., Zh. Organ. Khim. 1, 1877 (1965)Google Scholar
  89. Lozinskii, M. O., Lopatinskaya, N. A., and Pel’kis, P. S., Chem. Abstr. 64, 3411 (1966).Google Scholar
  90. 85.
    Lozinskii, M. O., and Pel’kis, P. S., Zh. Organ. Khim. 1, 1976 (1965)Google Scholar
  91. Lozinskii, M. O., and Pel’kis, P. S., Chem. Abstr. 64, 9619 (1966).Google Scholar
  92. 86.
    Lozinskii, M. O., and Pel’kis, P. S., Zh. Organ. Khim. 2, 692 (1966)Google Scholar
  93. Lozinskii, M. O., and Pel’kis, P. S., Chem. Abstr. 65, 8814 (1966).Google Scholar
  94. 87.
    Lozinskii, M. O., Sanova, S. N., and Pel’kis, P. S., Zh. Organ. Khim. 2, 1716 (1966)Google Scholar
  95. Lozinskii, M. O., Sanova, S. N., and Pel’kis, P. S., Chem. Abstr. 66, 85766 (1967).Google Scholar
  96. 88.
    Neber, P. W., and Wörner, H., Ann. 526, 173 (1936).Google Scholar
  97. 89.
    Pechmann, v. H., Ber. 27, 320 (1894).CrossRefGoogle Scholar
  98. 90.
    Pechmann, v. H., and Seeberger, L., Ber. 27, 2122 (1894).Google Scholar
  99. 91.
    Scott, F. L., Morrish, W. N., and Reilly, J., J. Org. Chem. 32, 692 (1957).CrossRefGoogle Scholar
  100. 92.
    Scott, F. L., and Holland, N. M., Proc. Chem. Soc. 106 (1962).Google Scholar
  101. 93.
    Scott, F. L., and Cronin, D. A., Tetrahedron Letters 715 (1963).Google Scholar
  102. 94.
    Scott, F. L., and Cronin, D. A., Chem. & Ind. (London) 1757 (1964).Google Scholar
  103. 95.
    Scott, F. L., and Aylward, J. B., Tetrahedron Letters 841 (1965).Google Scholar
  104. 96.
    Sharp, D. B., and Hamilton, C. S., J. Am. Chem. Soc. 68, 588 (1946).CrossRefGoogle Scholar
  105. 97.
    Stille, J. K., Harris, F. W., and Bedford, M. A., J. Heteroc. Chem. 3, 155 (1966).CrossRefGoogle Scholar
  106. 98.
    Stolle, R., J. Prakt. Chem. 85, 386 (1911).CrossRefGoogle Scholar
  107. 99.
    Vanghelovici, M., Bl. Soc. Chim. Romania 8, 20 (1926)Google Scholar
  108. Vanghelovici, M., Chem. Abstr. 20, 1341 (1928)Google Scholar
  109. Vanghelovici, M., Bl. Soc. Chim. Romania 9, 59 (1927).Google Scholar

Copyright information

© Plenum Press 1968

Authors and Affiliations

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

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