The chemistry of carbohydrazide and thiocarbohydrazide

Chemical Reviews

Volumn 70, Issue 1, 1970, Pages 111-149

  Kurzer, Frederick ^a   Wilkinson, Michael ^a  

^a ROYAL FREE AND UNIVERSITY COLLEGE MEDICAL SCHOOL   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ANTINEOPLASTIC AGENT; CENTRAL STIMULANT AGENT; ENZYME INHIBITOR; IMIDE; KETONE; THIOUREA; UREA;

CHEMISTRY; CYTOCHEMISTRY; OXIDATION REDUCTION REACTION; REVIEW; SYNTHESIS;

AMINES; ANTIBIOTICS; ANTIFUNGAL AGENTS; ANTINEOPLASTIC AGENTS; CENTRAL NERVOUS SYSTEM STIMULANTS; CHEMISTRY; ENZYME INHIBITORS; HISTOCYTOCHEMISTRY; IMIDES; KETONES; OXIDATION-REDUCTION; THIOUREA; UREA;

EID: 0014734997     PISSN: 00092665     EISSN: 15206890     Source Type: Journal    
DOI: 10.1021/cr60263a004     Document Type: Article

References (367)

1. T. Curtius and K. Heidenreich, Chem. Ber., 27, 55 (1894).
2. T. Curtius and K. Heidenreich, J. Prakt. Chem., [2] 52, 454 (1895).
3. R. Stollé and P. E. Bowles, Chem. Ber., 41, 1099 (1908).
4. E. E. Reid, “Organic Chemistry of Bivalent Sulphur,” Vol. V, Chemical Publishing Co. Inc., New York, N. Y., 1963: p 206.
5. E. E. Reid, “Organic Chemistry of Bivalent Sulphur,” Vol. V, Chemical Publishing Co. Inc., New York, N. Y., 1963: p 283.
6. C. C. Clarke, “Hydrazine,” Mathieson Chemical Corp., Baltimore, Md., 1953, p 75.
7. J. Sandström, Svensk Kem. Tidskr., 68, 131 (1956).
8. R. G. Dubenko and P. S. Pelkis, Zh. Obshch. Khim., 33, 290 (1963).
9. E. P. Nesynov and P. S. Pelkis, Zh. Obshch. Khim., 34, 2672 (1964).
10. L. F. Audrieth, E. S. Scott, and P. S. Kippur, J. Org. Chem., 19, 733 (1954).
11. L. F. Audrieth and B. A. Ogg, “The Chemistry of Hydrazine,” John Wiley and Sons, Inc., New York, N. Y., 1951, p 213.
12. J. F. Willems, Fortschr. Chem. Forsch., 4, 554 (1963);
13. Fortschr. Chem. Forsch., 5, 147 (1965).
14. W. Resting, Chem. Ber., 57, 1321 (1924).
15. W. Borsche, W. Müller, and C. A. Bodenstein, Ann., 475, 120 (1929).
16. E. B. Mohr, J. J. Brezinski, and L. F. Audrieth, Inorg. Syn., 4, 32 (1953).
17. Brazaitis and Tarika, “Chemical Engineering Progress Reports,” University of Illinois, 1949, quoted in ref 15.
18. P. Cazeneuve and P. Moreau, Compt. Rend., 129, 1254 (1899).
19. T. Lieser and G. Nischk, Chem. Ber., 82, 527 (1949).
20. O. Glemser, H. Weber, and H. Duyster, Z. Anorg. Allgem. Chem., 286, 205 (1956).
21. P. W. West and J. Warkentin, J. Org. Chem., 33, 2089 (1968).
22. D. N. Majumdar and P. C. Guha, J. Indian Chem. Soc., 10, 692 (1933).
23. R. Stollé and K. Hofmann, Chem. Ber., 37, 4523 (1904).
24. F. Fichter and B. Becker, Chem. Ber., 44, 3481 (1911).
25. C. S. Argyle (to Whiffen and Sons Ltd.), U. S. Patent 3,258,485 (1966);
26. Chem. Abstr., 65, 7067 (1966).
27. R. Stollé, Chem. Ber., 37, 3548 (1904).
28. W. Autenrieth and H. Hefner, Chem. Ber., 58, 2151 (1925).
29. P. C. Guha and S. C. De, J. Chem. Soc., 125, 1215 (1924).
30. N. Petri, Z. Naturforsch., 16B, 769 (1961); see also
31. S. M. Losanitch, J. Chem. Soc., 121, 2542 (1922).
32. L. F. Audrieth and P. S. Kippur (to University of Illinois Foundation), U. S. Patent 2,726,263 (1955);
33. Chem. Abstr., 50, 10128 (1956).
34. Olin Mathieson Chemical Corp., British Patent 754, 756 (1956);
35. Chem. Abstr., 51, 8782 (1957).
36. E. Hoggarth, J. Chem. Soc., 4817 (1952).
37. H. Beyer, W. Lässig, and U. Schultz, Chem. Ber., 87, 1401 (1954).
38. J. Sandström, Arkiv Kemi, 4, 297 (1952).
39. R. Mayer and K. Schafer, J. Prakt. Chem., 26, 279 (1964).
40. G. Beck, Wien Chemiker-Ztg., 46, 18 (1943);
41. Chem. Abstr., 39, 4593 (1945).
42. F. Kurzer and M. Wilkinson, unpublished work.
43. B. S. S. Rao and S. Soundararajan, Proc. Indian Acad. Sci., 50A, 149 (1959).
44. R. P. Smith, T. Ree, J. L. Magee, and H. Eyring, J. Am. Chem. Soc., 73, 2263 (1951).
45. M. Fedoroňko, O. Manoušek, and P. Zuman, Chem. Listy, 49, 1494 (1955);
46. Chem. Abstr., 50, 79 (1956).
47. R. Stollé and E. Gaertner, J. Prakt. Chem., 132, 209 (1931).
48. R. Glicksman, J. Electrochem. Soc., 110, 353 (1963).
49. S. Shuzuki and W. Takahashi, Denki-Kagaku, 33, 13 (1965);
50. Chem. Abstr., 65, 9783 (1966).
51. Sadtlerʼns Standard Spectra Catalogue, No. 5701, Sadtler Research Laboratories Inc., Philadelphia, Pa.
52. D. M. Wiles and T. Suprunchuck, Can. J. Chem., 46, 701 (1968).
53. C. M. Kraebel, S. M. Davis, and M. J. Landon, Spectrochim. Acta, 23A, 2541 (1967).
54. Beck, Thesis, University of Illinois, 1948, quoted in ref 15.
55. H. Beyer and C. F. Kroger, Ann., 637, 126 (1960).
56. A. H. Corwin and J. D. Reinheimer, J. Am. Chem. Soc., 73, 11 4 (1951).
57. W. K. McEwen, J. Am. Chem. Soc., 58, 1124 (1936).
58. F. Fehér and K. H. Linke, J. Prakt. Chem., 32, 190 (1966).
59. E. Colton, M. M. Jones, and L. F. Audrieth, J. Am. Chem. Soc., 76, 2572 (1954).
60. E. S. Scott and L. F. Audrieth, J. Org. Chem., 19, 1231 (1954).
61. A. C. Brown, E. C. Pickering, and F. J. Wilson, J. Chem. Soc., 107 (1927).
62. A. M. Munro and F. J. Wilson, J. Chem. Soc., 1257 (1928).
63. J. Szmuszkovicz and M. E. Greig, J. Med. Pharm. Chem., 4, 259 (1961).
64. R. G. Haber, U. S. Patent 3,231,570 (1966);
65. Chem. Abstr., 64, 9685 (1966).
66. P. Koschucharov and T. Harisanova, Pharmazie, 15, 492 (1960).
67. R. G. Haber (to ABIC Chemical Laboratories Ltd.), Belgian Patent 618, 951 (1962);
68. Chem. Abstr., 58, 11334 (1963).
69. ABIC Chemical Laboratories Ltd., British Patent 959, 130 (1964);
70. Chem. Abstr., 61, 9467 (1964).
71. A. Albert, German Patent 463, 313 (1928);
72. Chem. Abstr., 22, 4128 (1928).
73. F. J. Wilson and A. B. Crawford, J. Chem. Soc., 127, 103 (1925).
74. W. Borsche and C. Merkwitz, Chem. Ber., 37, 3177 (1904).
75. P. C. Guha and S. C. De, J. Indian Chem. Soc., 2, 225 (1926).
76. H. W. Stephen and F. J. Wilson, J. Chem. Soc., 2531 (1926).
77. N. P. Buu-Hoi, T. B. Loc, and N. D. Xuong, Bull. Soc. Chim, France, 694 (1955).
78. W. Ried and G. Oertel, Ann., 590, 136 (1954).
79. C. Runti, Ann. Chim. (Rome), 46, 731 (1956).
80. J. Sandström, Acta Chem. Scand., 14, 1037 (1960).
81. J. Sandström, Acta Chem. Scand., 14, 1939 (1960).
82. R. Riemschneider, B. Böttcher, and S. Georgi, Monatsh., 91, 630 (1960).
83. S. C. De, J. Indian Chem. Soc., 5, 373 (1928).
84. C. Liebermann, Chem. Ber., 16, 2858 (1883).
85. D. Hadži, J. Chem. Soc., 2143 (1956).
86. K. J. Morgan, J. Chem. Soc., 2151 (1961).
87. V. Bekárek, K. Rothschein, P. Vetesnik, and M. Večera, Tetrahedron Letters, 3711 (1968).
88. H. El-Khadem, Z. M. El-Shafei, and M. M. Hashem, J. Chem. Soc., C., 949 (1968).
89. E. H. Rodd, Ed., “The Chemistry of Carbon Compounds,” Vol. IVA, Elsevier Publishing Co., New York, N. Y., 1957, p 106.
90. H. W. Stephen and F. J. Wilson, J. Chem. Soc., 1415 (1928).
91. J. Warkentin and P. R. West, Tetrahedron Letters, 5815 (1966).
92. M. J. Harrison, R. O. C. Norman, and W. A. F. Gladstone, J. Chem. Soc., C., 735 (1967).
93. R. Duschinsky and H. Gainer, J. Am. Chem. Soc., 73, 4464 (1951).
94. T. R. Vakula, V. R. Rao, and V. R. Srinivasan, Current Sci., 35, 487 (1966).
95. G. Young and W. Eyre, J. Chem. Soc., 79, 54 (1901).
96. G. Valenti and F. Maggio, Ann. Chim. (Rome), 42, 18 (1952).
97. J. R. Bailey and A. T. McPherson, J. Am. Chem. Soc., 39, 1322 (1917).
98. M. Busch, “Festschrift zum 80. Geburtstag des Prinzregenten Luitpold von Bayern,” Band 4, Teil 2, Erlangen, 1901, p 165;
99. Chem. Zentr., 1, 937 (1901).
100. R. Stollé, J. Prakt. Chem., 75, 416, 423 (1907).
101. H. Beyer and C. F. Kroger, Ann., 637, 135 (1960).
102. C. F. Kroger, L. Hummel, M. Mutscher, and H. Beyer, Chem. Ber., 98, 3025 (1965).
103. M. Kuranari and H. Takeuchi (to Chugai Pharmaceutical Co. Ltd.), Japanese Patent 21, 420 (1965);
104. Chem. Abstr., 64, 2097 (1966).
105. L. F. Audrieth and E. B. Mohr, Inorg. Syn., 4, 29 (1953).
106. H. A. Staab, Angew. Chem. Intern. Ed. Engl., 1, 355 (1962).
107. Phrix Arbeitsgemeinschaft, German Patent 740, 829 (1943);
108. Chem. Abstr., 40, 600 (1946).
109. W. Lässig and E. Günther, German Patent 1,058,844 (1959);
110. Chem. Abstr., 55, 26806 (1961).
111. H. Weidinger and J. Kranz, Chem. Ber., 96, 1059, 1064 (1963).
112. C. F. Kröger, E. Tenor, and H. Beyer, Ann., 643, 121 (1961).
113. A. Dornow and H. Pietsch, Chem. Ber., 100, 2585 (1967).
114. A. Dornow, H. Menzel, and P. Marx, Chem. Ber., 97, 2173 (1964).
115. R. H. Hall, J. Am. Chem. Soc., 80, 1145 (1958).
116. P. C. Guha and S. C. De, J. Indian Chem. Soc., 1, 141 (1924).
117. H. Beyer, G. Wolter, and H. Lemke, Chem. Ber., 89, 2550 (1956).
118. H. Beyer and G. Wolter, Chem. Ber., 89, 1652 (1956).
119. J. Sandström, Acta Chem. Scand., 15, 1295 (1961).
120. P. F. Wiley in “The Chemistry of Heterocyclic Compounds,” A. Weissberger, Ed., Interscience Publishers, New York, N. Y., 1956, p 191.
121. V. P. Wystrach in “Heterocyclic Compounds,” Vol. 8, R. C. Elderfield, Ed., John Wiley and Sons Inc., New York, N. Y., 1967, p 135.
122. A. W. Lutz, J. Org. Chem., 29, 1174 (1964).
123. N. Petri, Z. Naturforsch., 16B, 767 (1961).
124. F. Arndt and E. Milde, Chem. Ber., 54, 2089 (1921).
125. L. Loewe and M. Türgen, Rev. Fac. Sci. Univ. Istanbul, 14A, 227 (1949);
126. Chem. Abstr., 44, 6415 (1950).
127. F. Arndt and F. Bielich, Chem. Ber., 56, 809 (1923).
128. J. Sandström, Acta Chem. Scand., 15, 1575 (1961).
129. K. Swincicki, R. Gompper, and W. Toepfl (to Farbenfabriken Bayer A. G.), Belgian Patent 617, 873 (1962);
130. Chem. Abstr., 59, 636 (1963).
131. T. Beckett and G. M. Dyson, J. Chem. Soc., 1358 (1937).
132. F. Kurzer, Chem. Ind. (London), 1333 (1961).
133. F. Kurzer and A. Lawson, Org. Syn., 42, 100 (1962).
134. H. B. König, W. Siefken, and H. A. Offe, Chem. Ber., 87, 825 (1954).
135. H. B. König and H. A. Offe (to Farbenfabriken Bayer A. G.), German Patent 953, 802 (1956);
136. Chem. Abstr., 53, 4309 (1959).
137. H. B. König and H. A. Offe (to Farbenfabriken Bayer A. G.), German Patent 953, 801 (1956);
138. Chem. Abstr., 53, 4309 (1959).
139. W. R. Sherman and A. von Esch, J. Org. Chem., 27, 3472 (1962);
140. U. S. Patent 3,058,988 (1962) (to Abbot Laboratories);
141. Chem. Abstr., 58, 9030 (1963).
142. A. Stempel, J. Zelauskas, and J. A. Aeschlimann, J. Org. Chem., 20, 412 (1955).
143. J. Sandström, Acta Chem. Scand., 17, 1595 (1963).
144. M. Kanaoka, J. Pharm. Soc. Japan. 76, 1133 (1956);
145. Chem. Abstr., 51, 3579 (1957).
146. G. Pellizzari and F. Roncagliolo, Gazz. Chim. Ital., 37I, 434 (1907).
147. L. F. Audrieth and E. B. Mohr, Inorg. Syn., 4, 36 (1953).
148. E. S. Scott and L. F. Audrieth, J. Org. Chem., 19, 742 (1954).
149. J. M. Stratton and F. J. Wilson, J. Chem. Soc., 1154 (1931).
150. A. Dornow and K. Fischer, Chem. Ber., 99, 72 (1966).
151. R. Huisgen, W. Mack, and E. Anneser, Angew. Chem., 73, 656 (1961).
152. R. Huisgen, Angew. Chem., 75, 604 (1963).
153. L. L. Bambas in “The Chemistry of Heterocyclic Compounds,” Vol. 4, A. Weissberger, Ed., Interscience Publishers, New York, N. Y., 1952, p 149 ff.
154. F. Arndt and F. Bielich, Chem. Ber., 56, 2276 (1923).
155. F. Arndt, E. Milde, and F. Tschenscher, Chem. Ber., 55, 349 (1922).
156. R. S. McElhinney, J. Chem. Soc., C., 1256 (1956).
157. F. Kurzer and M. Wilkinson, J. Chem. Soc., C., 2108 (1968).
158. A. Dornow and H. Paucksch, Chem. Ber., 99, 81 (1966).
159. C. Larsen and E. Binderup, Acta Chem. Scand., 21, 1984 (1967).
160. V. E. Bogachev (to Organisation of the State Committee for Defence, USSR), USSR Patent 174, 635 (1965);
161. Chem. Abstr., 64, 8047 (1966).
162. A. Dornow and H. Paucksch, Chem. Ber., 99, 85 (1966).
163. E. Hoggarth, J. Chem. Soc., 614 (1950).
164. H. Gehlen and G. Röbisch, Ann., 660, 148 (1962).
165. F. Kurzer and M. Wilkinson, J. Chem. Soc., C., 2099 (1968).
166. H. Ulrich, “Cycloaddition Reactions of Heterocumulenes,” Academic Press, New York, N. Y., 1967.
167. M. Busch and T. H. Ulmer, Chem. Ber., 35, 1721 (1902).
168. F. Kurzer and K. Douraghi-Zadeh, J. Chem. Soc., 3912 (1965);
169. C., 742 (1967).
170. F. Kurzer and M. Wilkinson, J. Chem. Soc., in press.
171. T. Curtius and K. Heidenreich, Chem. Ber., 27, 2684 (1894).
172. E. Lieber, R. L. Minnis, Jr., and C. N. R. Rao, Chem. Rev., 65, 377 (1965).
173. R. Stollé, Chem. Ber., 55, 1289 (1922).
174. F. Kurzer and K. Douraghi-Zadeh, Chem. Rev., 67, 108 (1967).
175. P. A. S. Smith, “The Chemistry of Open-Chain Organic Nitrogen Compounds,” Vol. II, W. A. Benjamin, Inc., New York, N. Y., 1966: p 243.
176. P. A. S. Smith, “The Chemistry of Open-Chain Organic Nitrogen Compounds,” Vol. II, W. A. Benjamin, Inc., New York, N. Y., 1966: p 127.
177. P. A. S. Smith, J. Am. Chem. Soc., 76, 436 (1954).
178. F. Eloy and C. Moussebois, Bull. Soc. Chim. Beiges, 68, 433 (1959).
179. P. F. Wiley, J. Am. Chem. Soc., 76, 5176 (1954).
180. S. J. Angyal and W. K. Warburton, J. Chem. Soc., 2492 (1951).
181. G. B. L. Smith and E. Anzelmi, J. Am. Chem. Soc., 57, 2730 (1935).
182. G. I. Keim, R. A. Henry, and G. B. L. Smith, J. Am. Chem. Soc., 72, 4944 (1950).
183. M. Freund and F. Kuh, Chem. Ber., 23, 2821 (1890).
184. S. Skinner and S. Ruhemann, J. Chem. Soc., S3, 550 (1888).
185. M. Mistry and P. C. Guha, J. Indian Chem. Soc., 7, 793 (1930).
186. P. C. Guha and M. A. Hye, J. Indian Chem. Soc., 7, 933 (1930).
187. M. M. J. Sutherland and F. J. Wilson, J. Chem. Soc., 125, 2145 (1924).
188. P. C. Guha and S. K. Roy-Choudhury, J. Indian Chem. Soc., 5, 149 (1928).
189. E. P. Nesynov and P. S. Pelkis, Dopovidi Akad. Nauk Ukr. RSR, 8, 1080 (1962);
190. Chem. Abstr., 58, 10, 117 (1963);
191. Zh. Org. Khim., 4, 837 (1968).
192. P. S. Pelkis and E. P. Nesynov, USSR Patent 165, 748 (1964);
193. Chem. Abstr., 62, 10384 (1965).
194. W. Baird and F. J. Wilson, J. Chem. Soc., 2367 (1926).
195. W. Baird and F. J. Wilson, J. Chem. Soc., 2114 (1927).
196. J. M. Sprague and A. H. Land in “Heterocyclic Compounds,” Vol. 5, R. C. Elderfield, Ed., John Wiley and Sons, New York, N. Y., 1957, pp 484, 512.
197. P. C. Guha and S. K. Roy-Choudhury, J. Indian Chem. Soc., 5, 163 (1928).
198. R. G. Dubenko and P. S. Pelkis, Zh. Obshch. Khim., 33, 2298 (1963);
199. J. Gen. Chem., 33, 2237 (1963).
200. F. Kurzer and M. Wilkinson, J. Chem. Soc., C., in press.
201. R. G. Dubenko, I. M. Bazavova, and P. S. Pelkis, Ukr. Khim. Zh., 33, 638 (1967);
202. Chem. Abstr., 67, 90736 (1967).
203. R. G. Dubenko and P. S. Pelkis, Zh. Obschch. Khim., 33, 2682 (1963);
204. J. Gen Chem., 33, 2612 (1963).
205. K. Ueno, J. Am. Chem. Soc., 74, 4508 (1952).
206. E. Klingsberg and D. Papa, J. Am. Chem. Soc., 73, 4988 (1951).
207. G. Schleitzer, Dissertation, University of Greifswald, Institute for Inorganic Chemistry, 1956.
208. J. Sandström, Arkiv Kemi, 9, 255 (1956).
209. J. Sandström, Acta Chem. Scand., 18, 871 (1964).
210. G. Losse, W. Hessler, and A. Barth, Chem. Ber., 91, 150 (1958).
211. L. Raphaelian, H. Hooks, and G. Ottmann, Angew. Chem. Intern. Ed. Engl, 6, 363 (1967);
212. U. S. Patent 3,304,327 (1967);
213. Chem. Abstr., 66, 75821 (1967).
214. U. Anthoni, C. Larsen, and P. H. Nielson, Acta Chem. Scand., 22, 309 (1968).
215. U. Anthoni, C. Larsen, and P. H. Nielson, Acta Chem. Scand., 21, 1201 (1967).
216. K. A. Jensen, J. Prakt. Chem., 159, 189 (1941).
217. F. C. Brown, C. K. Bradsher, B. F. Moser, and S. Forrester, J. Org. Chem., 24, 1056 (1959).
218. K. A. Jensen, U. Anthoni, B. Kägi, C. Larson, and C. T. Pedersen, Acta Chem. Scand., 22, 1 (1968).
219. R. Stollé and K. Krauch, Chem. Ber., 47, 724 (1914).
220. P. S. Pelkis and E. P. Nesynov, USSR Patent 170, 523 (1965);
221. Chem. Abstr., 63, 9823 (1965).
222. E. P. Nesynov and P. S. Pelkis, USSR Patent 179, 775 (1966);
223. Chem. Abstr., 65, 7102 (1966).
224. E. P. Nesynov and P. S. Pelkis, USSR Patent 179, 777 (1966);
225. Chem. Abstr., 65, 10544 (1966).
226. E. P. Nesynov and P. S. Pelkis, USSR Patent 179, 776 (1966);
227. Chem. Abstr., 65, 7102 (1966).
228. H. Gehlen and W. Schade, Naturwissenschaften, 46, 667 (1959).
229. O. Diels and H. Okada, Chem. Ber., 45, 2437 (1912).
230. O. Diels and A. Wagner, Chem. Ber., 45, 874 (1912).
231. O. Diels and H. Okada, Chem. Ber., 46, 1870 (1913).
232. R. Stollé and K. O. Leverkus, Chem. Ber., 46, 4076 (1913).
233. J. A. Aeschlimann (to Hoffmann-La Roche Inc.), U. S. Patent 2,665,279 (1954);
234. Chem. Abstr., 49, 2521 (1955).
235. E. P. Nesynov, M. M. Besprozvannaya, and P. S. Pelkis, Zh. Organ. Khim., 2, 25 (1966);
236. Soviet J. Org. Chem., 2, 21 (1966).
237. E. P. Nesynov, M. M. Besprozvannaya, and P. S. Pelkis, Zh. Organ. Khim., 2, 484 (1966);
238. Soviet J. Org. Chem., 2, 486 (1966).
239. P. S. Pelkis and E. P. Nesynov, USSR Patent 170, 524 (1965);
240. Chem. Abstr., 63, 9823 (1965).
241. E. P. Nesynov and P. S. Pelkis, Zh. Organ. Khim., 2, 459 (1966);
242. Soviet J. Org. Chem., 2, 460 (1966).
243. E. Hedaya, R. L. Hinman, and S. Theodoropulos, J. Org. Chem., 31, 1317 (1966).
244. E. Hedaya, R. L. Hinman, and S. Theodoropulos, J. Org. Chem., 31, 1311 (1966).
245. G. D. Buckley and N. H. Ray, J. Chem. Soc., 1156 (1949).
246. G. D. Buckley and N. H. Ray, British Patent 649, 445 (1951);
247. Chem. Abstr., 45, 8560 (1951).
248. H. J. Sampson Jr., U. S. Patents 2,589,289 and 2,589,290 (1952);
249. Chem. Abstr., 46, 11234 (1952).
250. H. Minato, R. Hisada, and M. Tanaka, Bull. Soc. Chem. Japan, 39, 2512 (1966).
251. W. R. McBride, R. A. Henry, and S. Skolnik, Anal. Chem., 23, 890 (1951).
252. W. R. McBride, R. A. Henry, and S. Skolnik, Anal. Chem., 25, 1042 (1953).
253. H. McKennis Jr. and A. S. Yard, U. S. Department of Commerce, Office of Technical Services, P. B. Report, 143, 914, (1957);
254. Chem. Abstr., 55, 17375 (1961).
255. H. Guérin, “Traité de Manipulation et dʼnAnalyse des Gaz,” Masson et Cie, Paris, 1952.
256. A. F. Krivis, E. S. Gazda, G. R. Supp, and P. S. Kippur, Anal. Chem., 35, 1955 (1963).
257. C. Duval and N. D. Xuong, Mikrochim. Acta, 747 (1956).
258. C. Duval and T. B. Loc, Mikrochim. Acta, 458 (1956).
259. C. Duval and T. B. Loc, Compt. Rend., 240, 1097 (1955).
260. E. Campi, G. Ostacoli, A. Vanni, and E. Casorati, Ric. Sci., Rend., Sez. A, 6, 341 (1964);
261. Chem. Abstr., 62, 15490 (1965);
262. B. Steiger, Mikrochem., 16, 193 (1934).
263. D. Williams and F. M. Nakhla, Bull. Inst. Mining Met., 533, 257 (1951);
264. Chem. Abstr., 45, 6956 (1951).
265. A. Albert, Experientia, 9, 370 (1953).
266. S. Fallab and H. Erlenmeyer, Helv. Chim. Acta, 36, 6 (1953).
267. A. F. Krivis, G. R. Supp, and R. L. Doerr, Anal. Chem., 37, 52 (1965).
268. A. F. Krivis, G. R. Supp, and R. L. Doerr, Anal. Chem., 38, 936 (1966).
269. A. M. Seligman, J. S. Hanker, H. L. Wasserkrug, and H. Dmochonski, J. Histochem. Cytochem., 13, 629 (1965).
270. A. M. Seligman, H. L. Wasserkrug, and J. S. Hanker, J. Cell Biol., 30, 424 (1966).
271. J. S. Hanker, C. Deb, H. L. Wasserkrug, and A. Seligman, Science, 152, 1631 (1966).
272. L. A. Sternberger, J. S. Hanker, E. J. Donati, J. P. Petrali, and A. M. Seligman, J. Histochem. Cytochem., 14, 711 (1966).
273. J. A. Gordon and W. P. Jencks, Biochemistry, 2, 47 (1963).
274. L. Levine, J. A. Gordon, and W. P. Jencks, Biochemistry, 2, 168 (1963).
275. E. Margoliash, A. Novogrodsky, and A. Schejter, Biochem. J., 74, 339 (1960).
276. C. J. D. Zarafonetis and J. P. Kalas, Proc. Soc. Exptl. Biol. Med., 105, 560 (1960);
277. Chem. Abstr., 55, 9657 (1961).
278. W. Schuler and E. Wyss, Arch. Intern. Pharmacodyn., 128, 431 (1960);
279. Chem. Abstr., 55, 11654 (1961).
280. T. E. Kartvelishvili, Soobshch. Akad. Nauk. Gruz., 24, 231 (1960);
281. Chem. Abstr., 55, 1912 (1961).
282. C. C. Pfeiffer, K. F. Killam, E. H. Jenney, and W. H. Marshall, Epilepsia, 3, 121 (1954);
283. Chem. Abstr., 49, 8507 (1955).
284. E. H. Jenney and C. C. Pfeiffer, J. Pharmacol. Exptl. Therap., 122, 110 (1958);
285. Chem. Abstr., 52, 6602 (1958).
286. E. W. Maynert and H. K. Kaji, J. Pharmacol. Exptl. Therap., 137, 114 (1962);
287. Chem. Abstr., 57, 11813 (1962).
288. H. L. Williams and R. G. Wiegand, J. Pharmacol. Exptl. Therap., 128, 344 (1960);
289. Chem. Abstr., 54, 11267 (1960).
290. W. L. Johnson and J. L. OʼnLeary, Arch, Neurol., 12, 113 (1965);
291. Chem. Abstr., 62, 9631 (1965).
292. B. L. Freedlander and A. Furst, Proc. Soc. Exptl. Biol. Med., 81, 638 (1952).
293. P. T. B. Loc, Compt. Rend. Soc. Biol., 160, 36 (1966).
294. R. Donovick, F. Pansy, G. Stryker, and J. Bernstein, J. Bacteriol., 59, 667 (1950).
295. J. I. Bruce and E. H. Sadun, Am. J. Trop. Med. Hyg., 15, 324 (1966);
296. Chem. Abstr., 65, 4467 (1966).
297. D. J. Smith, N. Y. State Dept. Health, Ann. Rept. Die. Lab. Res., 49 (1959);
298. Chem. Abstr., 54, 21401 (1960).
299. R. E. Cline and G. W. Pearce, J. Insect. Physiol., 12, 153 (1966).
300. H. W. Gausman, C. L. Rhykerd, H. R. Hinderliter, E. S. Scott, and L. F. Audrieth, Botan. Gaz., 114, 292 (1953);
301. Chem. Abstr., 47, 8955 (1953).
302. T. W. Campbell, V. S. Foldi, and J. Farago, J. Appl. Polymer Sci., 2, 155 (1959);
303. Chem. Abstr., 54, 11541 (1960).
304. H. Oertel and H. Rinke (to Farbenfabriken Bayer A. G.), Belgian Patent 621, 379 (1962);
305. Chem. Abstr., 59, 5347 (1963).
306. W. Thoma, H. Rinke, and H. Oertel, German Patent 1,150,517 (1963);
307. Chem. Abstr., 59, 8946 (1963).
308. Farbenfabriken Bayer A. G., Netherlands Appl., 6,410,335 (1965);
309. Chem. Abstr., 63, 13519 (1965).
310. Farbenfabriken Bayer A. G., Netherlands Appl., 6,412,962 (1965);
311. Chem. Abstr., 63, 13528 (1965).
312. E. I. DuPont de Nemours and Co., Netherlands Appl., 6, 508,384 (1965);
313. Chem. Abstr., 64, 16051 (1966).
314. H. Oertel, H. Rinke, F. K. Rosendahl, and H. Kleiner, Belgian Patent 648, 812 (1964);
315. Chem. Abstr., 64, 19903 (1966).
316. Farbenfabriken Bayer A. G., Netherlands Appl., 6,510,890 (1966);
317. Chem. Abstr., 65, 5639 (1966).
318. Farbenfabriken Bayer A. G., Netherlands Appl., 6,515,899 (1966);
319. Chem. Abstr., 65, 17179 (1966).
320. W. R. Grace and Co., British Patent 1,019,847 (1966);
321. Chem. Abstr., 64, 11396 (1966).
322. Phrix Arbeitsgemeinschaft, Belgian Patent 443,954 (1942);
323. Chem. Abstr., 39, 646 (1945).
324. Y. Inaba, K. Kimoto, Y. Miyake, and S. Hamatani, Japanese Patent 10, 046 (1957);
325. Chem. Abstr., 53, 8652 (1959).
326. T. Unishi and T. Tsujimura, Kogyo Kagaku Zasshi, 68, 2275 (1965);
327. Chem. Abstr., 64, 12811 (1966).
328. H. H. Levine, U. S. Patent 3,014,009 (1959);
329. Chem. Abstr., 56, 8932 (1962).
330. R. J. Thurmaier, U. S. Patent 3,149,998 (1964);
331. Chem. Abstr., 62, 734 (1965).
332. W. Thoma, Belgian Patent 660,945 (1965);
333. Chem. Abstr., 64, 2025 (1966).
334. Gevaert Photo-Production N. V., German Patent 1,023,969 (1958);
335. Chem. Abstr., 54, 15038 (1960).
336. Gevaert Photo-Production N. V., Belgian Patent 542,151 (1956);
337. Chem. Abstr., 54, 19244 (1960).
338. J. W. Britain (to General Aniline and Film Corp.), U. S. Patent 2,772,973 (1956);
339. Chem. Abstr., 51, 4188 (1957).
340. J. Kosar, U. S. Patent 3,157,503 (1964);
341. Chem. Abstr., 62, 2404 (1965).
342. E. M. Bickoff, A. L. Livingston, J. Guggolz, and C. R. Thompson, J. Am. Oil Chemistsʼn Soc., 29, 445 (1952);
343. Chem. Abstr., 47, 829 (1953).
344. R. C. Harshman and V. C. Fusco, U. S. Patent 2,963,438 (1960);
345. Chem. Abstr., 55, 5997 (1961).
346. D. W. Clayton and L. M. Marraccini, Svensk Papperstid., 69, 311 (1966);
347. Chem. Abstr., 65, 9160 (1966).
348. D. W. Ryker, U. S. Patent 2,970,899 (1961);
349. Chem. Abstr., 55, 10892 (1961).
350. Riedel and Co., British Patent 985, 316 (1965);
351. Chem. Abstr., 63, 1558 (1965).
352. R. G. Dubenko, I. M. Bazavova, and P. S. Pelkis, Zh. Org. Khim., 4, 1057 (1968);
353. Chem. Abstr., 69, 43841 (1968): structure 365 given therein lacks a double bond.
354. R. G. Dubenko, I. M. Bazavova, and P. S. Pelkis, USSR Patent 206, 581 (1967);
355. Chem. Abstr., 69, 52123 (1968).
356. J. M. Sprague and A. H. Land, “Heterocyclic Compounds,” Vol. 5, R. C. Elderfield, Ed., John Wiley and Sons, Inc., New York, N. Y., 1957, pp 484, 496.
357. R. G. Dubenko, I. M. Bazavova, and P. S. Pelkis, Ukr. Khim. Zh., 10, 1038 (1968).
358. R. N. Hurd and G. De la Mater, Chem. Rev., 61, 66 (1961);
359. E. Papadopoulos, J. Org. Chem., 31, 3060 (1966).
360. H. Gehlen and P. Demin, Z. Chem., 8, 221 (1968).
361. R. S. Varma, J. Indian Chem. Soc., 43, 558 (1966).
362. F. Kurzer and M. Wilkinson, J. Chem. Soc., C., 1218 (1969).
363. E. Hoggarth, J. Chem. Soc., 4811 (1952).
364. M. Kanaoka, J. Pharm. Soc. Japan, 76, 1133 (1956);
365. Chem. Abstr., 51, 3579 (1957).
366. A. P. Grekov and D. K. Yarovoi, Zh. Anal. Khim., 21, 1276 (1966);
367. Chem. Abstr., 66, 25933 (1967).