Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives / Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia University

by Yü-Gwan Chen

Coupler	Diazo. monoamine	On silk	Diazo. diamine	On silk
Phenol	deep red (alk)	v. light yellow	(alk) deep red	yellow
Dimethylaniline	orange (acid)	light yellow	orange-red (acid)	yellow
P-nitraniline	light brown (acid)		brownish (acid)	grayish brown
P-toluidine	light brown (acid)		brownish (acid)	brownish
Pyrogallic acid	dark brown (acid)	grayish	dark brown (alk)	grayish
Salicylic acid	reddish (alk)	light brown	red (alk)	brown
B-naphthol	deep red (alk)	pink	deep red (alk)	red
Sulphanilic acid	light brown (alk)	brownish	brown (alk)	brown
A-naphthylamine	light brown (acid)	brownish	yellow (acid)	yellow
Resorcinol	purple (alk)	red	dark purple (alk)	deep red

---

[BIBLIOGRAPHY]

1. Berzelius, Annales de Physique et Chimie (2) 9, 239, 356 (1818).
2. Gmelin-Kraut, “Handbuch der Anorg. Chemie” I (1) 705-804; Roscoe and Schorlemmer, “Treatise on Chemistry” I, 467-82 (1920); Browning, “Introduction to the Rarer Elements,” 144-52 (1917).
3. Victor Lenher, J. Ind. Eng. Chem., 12, 597 (1920).
4. Le Seleneum et ses applications actuelles, Chimie et Industrie (1919) 245.
5. C. R. Boggs, U. S. A., 1,249,272; J. Ind. Eng. Chem. 10, 117-8 (1918).
6. Duhamel & Robiere, Compt. rend. soc. biol. 72, 670 (1913); Am. Chem. Abs. 7, 2624 (1913).
7. B. G. Duhamel, Compt. rend. soc. biol., 72, 865 (1913); Am. Chem. Abs. 7, 2971 (1913).
8. Duhamel & Juillard, Compt. rend. soc. biol., 72, 714 (1913); Am. Chem. Abs., 7, 2624 (1913).
9. B. G. Duhamel, Compt. rend. soc. biol., 82, 724-6 (1919); Am. Chem. Abs. 14, 2383 (1920).
10. Wassermann, D. R. P., 261,556; 286,950; 287,020.
11. A. v. Wassermann, Keyser, & M. Wassermann, Duet. Med. Woch., 37, 2389 (1911); Am. Chem. Abs., 6, 650 (1912).
12. A. v. Wassermann & Hansmann, Berl. klin. Woch., 49, 4, (1911); Am. Chem. Abs., 6, 890 (1912).
13. Anthraquinone dyes, D. R. P., 256,667.
14. P. Ehrlich & H. Bauer, Ber., 48, 502 (1915).
15. Berzelius, Lehrbuch (5 Aufl.) 2, 213; Roscoe and Schorlemmer, “Treatise on Chemistry,” I, 473 (1920).
16. Bruere, J. Anat. Physiol., Oct., (1891).
17. T. W. Clarke & W. H. Hurtley, J. Physiol., 36, 62 (1907).
18. Hugo Bauer, Ber., 47, 1873 (1914).
19. Ehrlich & Guttmann, Berl. klin. Woch. (1891) 28; U. S. Disp., 20th Edition.
20. P. Karrer, 49, 597 (1916); Ber., 51, 190 (1918).
21. Hugo Bauer, Ber., 47, 1873 (1914); D. R. P., 261,969; Friedl., 11, 1124 (1913).
22. Selenazines, D. R. P., 280,713; 261,793.
23. U. S. Disp., 20th Edition.
24. D. R. P., 305,262; 305,263; Am. Chem. Abs., 13,325 (1918).
25. Bull. soc. chim., 41, 599; Compt. rend., 99, 1154-7 (1885); Brit. Chem. Abs., 50, 376 (1885); A. Ch., (6) 9, 294, 303, 323.
26. W. Baringer, Ber., 23, 1003 (1889).
27. P. Spica, Gazz. chim. ital., 7, 90-9 (1877); Brit. Chem. Abs., (1877) II, 189; Compt. rend., 99, 1154 (1884); 100, 1296 (1885); Frerichs, Arch. Pharm., 241, 180, 196; Beil., (1921) III, 295, 261.
28. C. Paal, Ber., 18, 2255 (1885); Gazz. chim. ital., (I. Zoppellari) 24, II, 399, (1894).
29. Ida Foa, Gazz. Chim. ital., 39, II, 527, (1909); C-B., (1910) I, 837.
30. D. R. P., 264,139.
31. O. Hinsberg, Ber., 22, 862, 2895 (1889); D. R. P., 261,412.
32. J. prakt. Chem., (1904) II, 69, 509.
33. E. Abderhalden, Hand. Biol. Chem., III, 2, 954.
34. Hanzlik & Tarr, Am. Univ. Ezpt. Sta., J. Pharmacol, 14, 221-8 (1919).
35. Hochst, D. R. P., 299,510.
36. D. R. P., 264,940; 264,961.
37. A. Michaelis & M. Stein, Ann., 320, 32 (1902).
38. Bogert & Hand, J. Am. Chem. Soc., 25, 377 (1902).
39. B. Bathke, Ann., 152, 210 (1869); Ann., 185, 331; Richter, Organische Chemie, I, 166.
40. Lesser & Schoeller, Ber., 47, 2293 (1914).
41. Lesser & Weiss, Ber., 45, 1835 (1912); 46, 2653, (1913).
42. Wohler & Dean, Ann., 97, 5 (1856); B. Rathke, Ann., 152, 211 (1869).
43. Cahours, Ann., 61, 92, (1847); 92, 356.
44. H. Klinger, Ber., 32, 2195, (1899); Ann., 119, 91; 121, 108.
45. C. A. Joy, Ann., 86, 35, (1853); B. Rathke, Ann., 152, 212, 219 (1869).
46. Wheeler, Z. Chem., (1867) 436.
47. Krafft & Lyons, Ber., 27, 1762 (1894); A. Ch., (6), 20, 228.
48. K. A. Hoffmann, Ber., 27, 2809 (1894).
49. M. Busch, Ber., 25, 2853, (1892).
50. Lellmann & Stickel, Ber., 19, 1605 (1886).
51. B. Rathke, Ann., 152, 201 (1869).
52. Gabriel & Stelzner, Ber., 29, 1313 (1896).
53. Bogert, Breneman, & Hand, J. Am. Chem. Soc., 25, 373 (1903).
54. Am. Chem. Abs., 3, 870 (1903); Bull. Belg. Soc. Chem., 23, 9-11.
55. Bogert & Hand, J. Am. Chem. Soc., 24, 1035, (1902).
56. Becker & Meyer, Ber. 37, 2551 (1914).
57. H. Bauer, Ber. 48, 507 (1915); Lyons & Shinn, J. Am. Chem. Soc. 1902: 1092; Fritz von Konek & O. Schleifer, Ber. 51, 850 (1918); A. Michaelis, Ber. 30, 2827 (1897); Ber. 48, 873 (1915); H. Frerichs, Arch. Pharm. 1902: 240, 656.
58. Fromm & Martin, Ann., 401, 178 (1913).

---

[VITA]

Yü-Gwan Chen was born in Nanking, China, March 8, 1893. After graduation from college in 1915, he further studied Chinese classics, 1915-16. He entered Case School of Applied Science, Cleveland, Ohio, as a special student in the Department of Chemistry, 1916-17. He registered at Columbia University to pursue graduate work in chemistry under the Faculty of Pure Science; and was awarded the degree of Master of Arts in 1918. From September 1919 to June 1922, he has been pursuing research in organic chemistry in the research laboratories of Havemeyer Hall, Columbia University.

FOOTNOTES: