Dimerization of anilines and benzylamines with mercury(II) oxide-iodine reagent

Tetrahedron

Volumn 54, Issue 29, 1998, Pages 8403-8410

  Onto, Kazuhiko ^a   Hatakeyama, Takahiro ^a   Uchiito, Shiho ^a   Tokuda, Masao ^a   Suginome, Hiroshi ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANILINE DERIVATIVE; AZOBENZENE DERIVATIVE; BENZYLAMINE; DICHLOROMETHANE; ETHYL PHENYLGLYCINATE; IODINE; MERCURIC OXIDE; N BENZHYDRYLIDENEBENZHYDRALYAMINE; N BENZYLIDENEBENZYLAMINE; REAGENT; UNCLASSIFIED DRUG;

ARTICLE; BINDING COMPETITION; CHEMICAL BINDING; DIMERIZATION; ENZYME SPECIFICITY; ENZYME SUBSTRATE; IODINATION; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0032537676     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00461-X     Document Type: Article

References (70)

1. 1. Orito, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis 1995, 1273-1277.
2. 2. Orito, K.; Hatakeyama ,T.; Takeo, M.; Takeo. M.; Suginome. H.; Tokuda, M. Synthesis 1997, 23-25.
3. 3. Orito, K.; Hatakeyama, T.; Takeo, M.; Uchiito. S.; Tokuda, M.; Suginome, H. Heterocyclic Commun. 1997, 3, 207-210.
4. 4. Orito, K.; Hatakeyama, T.; Takeo, M.; Suginome, H. Synthesis 1995, 1357-1358.
5. 5. Hedayatullah, M.; Dechatre, J. P.; Denivelle, L. Tetrahedron Lett. 1975, 25, 2039-2042.
6. 6. Fetizon. M.; Golfier, M.; Milcent. R.; Papadakis, I. Tetrahedron 1975, 31, 165-170.
7. 7. Ortiz, B.; Villanueva, P.; Walls, F. J. Org. Chem. 1972, 37, 2748-2750.
8. 8. Firouzabadi, H.; Vessal, B.; Naderi, M. Tetrahedron Lett. 1982, 23, 1847-1850.
9. 9. Nakagawa, K.; Tsuji ,T. Chem. Pharm. Bull. 1963, 11, 296-301.
10. 10. Barakat, M. Z.; Abdel-Wahab, M. F.; El-Sadr, M. M. J. Chem. Soc. 1956, 4685-4687.
11. 11. Wheeler, O. H.; Gonzalez, D. Tetrahedron 1964, 20, 189-193.
12. 12. Bhamagar, I.; George, M. V. J. Org. Chem. 1968, 33, 2407-2411. See ref. 18 also.
13. 13. Mehta, S. M.; Vakilwala, M. V. J. Am. Chem. Soc. 1952, 74, 563-564.
14. 14. Santurri. P.; Robbins. F.; Stubbings, R. Org. Synth. Coll. Vol. 5, 1973: pp. 341-343.
15. 15. Ogata, Y.; Shimizu, H. Bull. Chem. Soc. Jpn. 1979, 52, 635-636.
16. 16. Pausacker, K. H.; Scroggie, J. G. J. Chem. Soc. 1954, 4003-4006.
17. 17. Baer, E.; Tosoni, A. L. J. Am. Chem. Soc. 1956, 78, 2857-2858.
18. 18. Firouzabadi H, Mostafavipoor Z. Bull. Chem. Soc. Jpn. 1993, 56, 914-917.
19. 19. Firouzabadi, H.; Iranpoor, N. Synth. Commun. 1984, 14, 875-882.
20. 20. Firouzabadi, H.; Sardarian, A. R.; Naderi, M.; Vessal, B. Tetrahedron 1984, 40, 5001-5004.
21. 21. Knabe, J.; Roloff H. Chem. Ber. 1964, 97, 3452-3455.
22. 22. Crank, G.; Makin, M. I. H. Aust. J. Chem. 1984, 37, 845-855.
23. 23. Pausacker, K. H. J. Chem. Soc. 1953,1989-1990.
24. 24. Horner, L.; Dehnert, J. Chem. Ber. 1963, 96, 786-797.
25. 25. Terent'ev, A. P.; Mogilyanskif, Y. D. Doklady Akad. Nauk SSSR. 1955, 103, 91-93; Chem. Abst. 1956, 50, 4807e.
26. 25. Terent'ev, A. P.; Mogilyanskif, Y. D. Doklady Akad. Nauk SSSR. 1955, 103, 91-93; Chem. Abst. 1956, 50, 4807e.
27. 26. Kinoshita, K. Bull. Chem. Soc. Jpn. 1959, 32, 777-780, 780-783.
28. 27. Ghedini, M.; Pucci, D.; Neve F. Chem. Commun. 1996, 137-138.
29. 28. Belew, J. S.; Garza, C.; Mathieson, J. W. Chem. Commun. 1970, 634-635.
30. 29. Hughes, G. M. K.; Saunders, B. C. J. Chem. Soc. 1954, 4630-4634.
31. 30. Nitoshin, G. I.; Troyanskii, E. I.; Ioffe, V. A. Izv. Akad. Nauk SSSR. 1982, 2758-2762; Chem. Abstr. 1983, 98, 142897v.
32. 30. Nitoshin, G. I.; Troyanskii, E. I.; Ioffe, V. A. Izv. Akad. Nauk SSSR. 1982, 2758-2762; Chem. Abstr. 1983, 98, 142897v.
33. 31. Hudlicky, M. "Oxidations in Organic Chemistry", ACS Monograph 186, 1990: pp. 234-242.
34. 32. Cohen, S. G.; Wang, C. H. J. Am. Chem. Soc. 1955, 77, 2457-2460.
35. 33. Bacon, R. G. R.; Stewart, D. J. Chem. Soc. C 1966, 1384-1387.
36. 34. Rawalay, S. S.; Shchter, H. J. Org. Chem. 1967, 32, 3129-3131.
37. 35. Audette, R. J.; Quail, J. W.; Smith, P. J. Tetrahedron Lett. 1971, 279-282.
38. 36. Tsuda, Y.; Nakajima, S. Chem. Lett. 1978, 1397-1398.
39. 37. Clarke, T. G.; Hampson, N. A.; Lee, J. B.; Morley, J. R.; Scanlon, B. Tetrahedron Lett. 1968, 5685-5688.
40. 38. Castedo, L.; Riguer, R.; Rodrigues, M. J. Tetrahedron 1982, 38, 1569-1570.
41. 39. Neumann, R.; Levin, M. J. Org. Chem. 1991, 56, 5707-5710.
42. 40. Lee, G. A.; Freedman, H. H. Tetrahedron Lett. 1976, 1641-1644.
43. 41. Stojiljkovic, A.; Andrejevic, V.; Mihailovic, M. L. Tetrahedron, 1967, 23, 721-732.
44. 42. Kashdan, D. S.; Schwarte, J. A.; Rapoport, H. J. Org. Chem. 1982, 47, 2638-2643.
45. 43. Battersby, A. R.; Binks, R. J. Chem. Soc. 1958, 4333-4339.
46. 44. Wenkert, E; Wickberg, B. J. Am. Chem. Soc. 1962, 84, 4914-4919.
47. 45. Mihailovic, M. L.; Stojiljkovic, A.; Andrejevic, V. Tetrahedron Lett. 1965, 461-464.
48. 46. Schröder, M.; Griffith, W. P. Chem Commun. 1979, 58-59.
49. 47. Shechter, H.; Rawalay, S. S. J. Am. Chem. Soc. 1964, 86, 1706-1709.
50. 48. For PhIO, see Müller. P.; Gilabert, N. Tetrahedron 1988, 44, 7171-7175.
51. 2, see Murahashi, S.; Naota, R.; Taki, H. J. Chem. Soc. Chem. Commun. 1985, 613-614.
52. 50. For Pd, see Murahashi, S.; Yoshimura, N.; Tsumiyama, T.; Kojima, T. J. Am. Chem. Soc. 1983, 105, 5002-5011.
53. 51. Bacon J, Adams RN. J. Am. Chem. Soc. 1968; 90: 6596-6599, and ref. 30.
54. 52. Nelson RF. "Anodic Oxidation of Pathways of Aliphatic and Aromatic Nitrogen Functions" in Technique of Electroorganic Synthesis, Part 1 (Technique of Chemistry, Vol. 5), Weinberg, NL. Ed. John Wiley & Sons, 1974: pp. 535-792.
55. 53. Onto, K.; Satoh, S.; Suginome, H. Chem. Commun. 1989, 1829-1831.
56. 54. Onto, K.; Ohio, M.; Suginome, H. Chem. Commun. 1990, 1074-1076; 1076-1078.
57. 55. Onto, K.; Ohto, M.; Sugawara, M.; Suginome, H. Tetrahedron Lett. 1990, 31, 5921-5924.
58. 56. Orito, K.; Yorita, K.; Suginome, H. Tetrahedron Lett. 1991, 32, 5999-6002.
59. 57. Suginome, H.; Orito, K.; Yorita, K.; Ishikawa, M.; Shimoyama, N.; Sasaki, T. J. Org. Chem. 1995, 60, 3025-3064.
60. 58. Orito, K.; Sato, S.; Suginome, H. J. Chem. Soc. Perkin Trans, 1 1995, 63-67.
61. 59. Orito, K.; Sasaki, T.; Suginome, H. J. Org. Chem. 1995, 60, 6208-6210.
62. 60. Sasaki, Y.; Olsen, F. P. Can. J. Chem. 1971, 49, 271 -282.
63. 61. Satomi, Y.; Taira, S.; Hata, K. Nippon Kagaku Zasshi, 1958, 79, 1298-1301; Chem. Abstr. 1960,54, 5552f.
64. 61. Satomi, Y.; Taira, S.; Hata, K. Nippon Kagaku Zasshi, 1958, 79, 1298-1301; Chem. Abstr. 1960,54, 5552f.
65. 62. Kenner, G. W.; Robinson, J. T.; Tylor, C. M. B.; Webster, B. R. J. Chem. Soc. 1962, 1756-1762.
66. 63. Pelletier, J. C.; Cava, M. R J. Org. Chem. 1987, 52, 616-622.
67. 64. Ibata, T.; Yamashita, T.; Kashiuchi, M.; Nakano, S.; Nakawa, H. Bull. Chem. Soc. Jpn. 1984, 57, 2450-2455.
68. 65. Sugimori, S. Nippon Kagaku Zasshi 1971, 92, 426-428; Chem. Abstr. 1972, 76, 24814p.
69. 65. Sugimori, S. Nippon Kagaku Zasshi 1971, 92, 426-428; Chem. Abstr. 1972, 76, 24814p.
70. 66. Scheppele, S. E.; Grizzle, P. L; Miller, D. W. J. Am. Chem. Soc. 1975, 97, 6165-6169.