Trapping of carbamic acid species with (trimethylsilyl)diazomethane

Tetrahedron

Volumn 62, Issue 1, 2006, Pages 226-235

  Ito, Yoshikatsu ^a   Ushitora, Hiromi ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

(Trimethylsilyl)diazomethane; Amine; Carbamic acid; Carbon dioxide; Methyl carbamate

Indexed keywords

(TRIMETHYLSILYL)DIAZOMETHANE; BENZENE; CARBAMIC ACID DERIVATIVE; CARBAMIC ACID METHYL ESTER; CARBON DIOXIDE; DIAZONIUM COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; ATMOSPHERIC PRESSURE; CARBONYLATION; PRIORITY JOURNAL; REACTION ANALYSIS; ROOM TEMPERATURE; SEPARATION TECHNIQUE; TEMPERATURE SENSITIVITY;

EID: 28444470471     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2005.09.116     Document Type: Article

References (79)

1. K. Masuda, Y. Ito, M. Horiguchi, and H. Fujita Tetrahedron 61 2005 213 229
2. Y. Ito Photochemistry 33 2002 205 212
3. D.M. Rudkevich, and H. Xu J. Chem. Soc. 2005 2651 2659
4. E.M. Hampe, and D.M. Rudkevich J. Chem. Soc. 2002 1450 1451
5. K. Izutsu Electrochemistry in Nonaqueous Solutions 2002 Wiley-VCH Weinheim Chapter 3
6. N. Hashimoto, T. Aoyama, and T. Shioiri Chem. Pharm. Bull. 29 1981 1475 1478
7. T. Shioiri, and T. Aoyama Yuki Gosei Kagaku Kyokai Shi 44 1986 149 159
8. T. Shioiri, and T. Aoyama Yuki Gosei Kagaku Kyokai Shi 54 1996 918 928
9. D.B. Dell'Amico, F. Calderazzo, L. Labella, F. Marchetti, and G. Pampaloni Chem. Rev. 103 2003 3857 3897
10. Esterification of carbamic acid with alkyl halide. (a) E.R. Pérez, R.H.A. Santos, M.T.P. Gambardella, L.G.M. de Macedo, U.P. Rodrigues-Filho, J.-C. Launay, and D.W. Franco J. Org. Chem. 69 2004 8005 8011
11. Also see, D.J. Heldebrant, P.G. Jessop, C.A. Thomas, C.A. Eckert, and C.L. Liotta J. Org. Chem. 70 2005 5335 5338
12. E.R. Prez, M.O. da Silva, V.C. Costa, U.P. Rodrigues-Filho, and D.W. Franco Tetrahedron Lett. 43 2002 4091 4093
13. R.N. Salvatore, F. Chu, A.S. Nagle, E.A. Kapxhiu, R.M. Cross, and K.W. Jung Tetrahedron 58 2002 3329 3347
14. R.N. Salvatore, S.I. Shin, A.S. Nagle, and K.W. Jung J. Org. Chem. 66 2001 1035 1037
15. M. Yoshida, N. Hara, and S.J. Okuyama J. Chem. Soc. 2000 151 152
16. W. McGhee, D. Riley, K. Christ, Y. Pan, and B. Parnas J. Org. Chem. 60 1995 2820 2830
17. M. Aresta, and E. Quaranta J. Chem. Soc., Dalton Trans. 1992 1893 1899
18. M. Aresta, and E. Quaranta Tetrahedron 48 1992 1515 1530
19. Y. Yoshida, S. Ishii, M. Watanabe, and T. Yamashita Bull. Chem. Soc. Jpn. 62 1989 1534 1538
20. Y. Hori, Y. Nagano, J. Nakao, T. Fukuhara, and H. Taniguchi Chem. Express 1 1986 224 227
21. Y. Yoshida, S. Ishii, and T. Yamashita Chem. Lett. 1984 1571 1572
22. Esterification of carbamic acid with alcohol. (a) C.J. Dinsmore, and S.P. Mercer Org. Lett. 6 2004 2885 2888
23. M. Feroci, A. Gennaro, A. Inesi, M. Orsini, and L. Palombi Tetrahedron Lett. 43 2002 5863 5865
24. M. Abla, J.-C. Choi, and T. Sakakura J. Chem. Soc. 2001 2238 2239
25. Y. Kubota, M. Kodaka, T. Tomohiro, and H. Okuno J. Chem. Soc., Perkin Trans. 1 1993 5 6
26. M. Kodaka, T. Tomohiro, and H. Okuno J. Chem. Soc., Chem. Commun. 1993 81 82
27. Esterification of carbamic acid with carbonate ester. (a) M. Selva, P. Tundo, A. Perosa, and F. Dall'Acqua J. Org. Chem. 70 2005 2771 2777
28. M. Selva, P. Tundo, and A. Perosa Tetrahedron Lett. 43 2002 1217 1219
29. M. Aresta, and A. Dibenedetto Chem. Eur. J. 8 2002 685 690
30. M. Aresta, and E. Quaranta Tetrahedron 47 1991 9489 9502
31. S. Ishii, H. Nakayama, Y. Yoshida, and T. Yamashita Bull. Chem. Soc. Jpn. 62 1989 455 458
32. Addition of carbamic acid to alkene, alkyne, or epoxide. (a) Y. Yoshida, and S. Inoue Chem. Lett. 1977 1375 1376
33. Q. Zhang, F. Shi, Y. Gu, J. Yang, and Y. Deng Tetrahedron Lett. 46 2005 5907 5911
34. M. Shi, and Y.-M. Shen J. Org. Chem. 67 2002 16 21
35. Y. Kayaki, T. Suzuki, Y. Noguchi, S. Sakurai, M. Imanari, and T. Ikariya Chem. Lett. 2002 424 425
36. A. Bacchi, G.P. Chiusoli, M. Costa, B. Gabriele, C. Righi, and G. Salerno J. Chem. Soc. 1997 1209 1210
37. C. Bruneau, and P.H. Dixneuf J. Mol. Catal. 74 1992 97 107 and references cited therein
38. F. Kojima, T. Aida, and S. Inoue J. Am. Chem. Soc. 108 1986 391 395
39. Y. Yoshida, and S. Inoue J. Chem. Soc., Perkin Trans. 1 1979 3146 3150
40. Y. Yoshida, and S. Inoue Chem. Lett. 1978 139 140
41. T. Asano, N. Saito, S. Ito, K. Hatakeda, and T. Toda Chem. Lett. 1978 311 312
42. T. Toda Chem. Lett. 1977 957 958
43. R.H. (Dopamine) Roth, F.I. Tarazi, and R.J. (Dopamine receptors) Baldessarini G. Adelman B.H. Smith Encyclopedia of Neuroscience Vol 1 1999 Elsevier Amsterdam 557 561 see also pp 561-565
44. Y. Ito, S. Horie, and Y. Shindo Org. Lett. 3 2001 2411 2413
45. Y. Ito, and S. Arimoto Phys. Org. Chem. 16 2003 849 857
46. P. Manini, L. Panzella, A. Napolitano, and M. d'Ischia Tetrahedron 59 2003 2215 2221
47. A. Napolitano, A. Palumbo, and M. d'Ischia Tetrahedron 56 2000 5941 5945
48. A. Napolitano, A. Pezzella, and G. Prota Chem. Res. Toxicol. 12 1999 1090 1097
49. A. Palumbo, A. Napolitano, P. Barone, and M. d'Ischia Chem. Res. Toxicol. 12 1999 1213 1222
50. A. Napolitano, A. Pezzella, and G. Prota Tetrahedron Lett. 40 1999 2833 2836
51. A. Pezzella, M. d'Ischia, A. Napolitano, G. Misuraca, and G. Prota J. Med. Chem. 40 1997 2211 2216
52. A. Napolitano, O. Crescenzi, A. Pezzella, and G. Prota J. Med. Chem. 38 1995 917 922
53. O. Crescenzi, C. Kroesche, W. Hoffbauer, M. Jansen, A. Napolitano, G. Prota, and M.G. Peter Liebigs Ann. Chem. 1994 563 567
54. G. Prota, M. d'Ischia, and A. Napolitano J.J. Nordlund R.E. Boissy V.J. Hearing R.A. King J.P. Ortonne The Pigmentary System 1998 Oxford University Press New York Chapter 24
55. G.N.L. Jameson, A.B. Kudryavtsev, and W. Linert J. Chem. Soc., Perkin Trans. 2 2001 557 562
56. U. El-Ayaan, E. Herlinger, R.F. Jameson, and W. Linert J. Chem. Soc., Dalton Trans. 1997 2813 2818
57. W. Linert, E. Herlinger, R.F. Jameson, E. Kienzl, K. Jellinger, and M.B.H. Youdim Biochim. Biophys. Acta 1316 1996 160 168
58. E. Herlinger, R.F. Jameson, and W. Linert J. Chem. Soc., Perkin Trans. 2 1995 259 263
59. A. Slivka, and G. Cohen J. Biol. Chem. 260 1985 15466 15472
60. E.J. Land, A. Perona, C.A. Ramsden, and P.A. Riley Org. Biomol. Chem. 3 2005 2387 2388
61. E.J. Land, C.A. Ramsden, and P.A. Riley Acc. Chem. Res. 36 2003 300 308
62. P.G. Jessop, D.J. Heldebrant, X. Li, C.A. Eckert, and C.L. Liotta Nature 436 2005 1102
63. P. Munshi, A.D. Main, J.C. Linehan, C.-C. Tai, and P.G. Jessop J. Am. Chem. Soc. 124 2002 7963 7971
64. K.N. West, C. Wheeler, J.P. McCarney, K.N. Griffith, D. Bush, C.L. Liotta, and C.A. Eckert J. Phys. Chem. A 105 2001 3947 3948
65. R.K. Khanna, and M.H. Moore Spectrochim. Acta 55A 1999 961 967
66. M. Aresta, and E. Quaranta Tetrahedron 48 1992 1515 1530
67. M. Caplow J. Am. Chem. Soc. 90 1968 6795 6803
68. S.L. Johnson, and D.L. Morrison J. Am. Chem. Soc. 94 1972 1323 1334
69. S.P. Ewing, D. Lockshon, and W.P. Jencks J. Am. Chem. Soc. 102 1980 3072 3084
70. J.E. Crooks, and J.P. Donnellan J. Chem. Soc., Perkin Trans. 2 1989 331 333
71. B.N. Kozhushko, A.V. Lomakina, Y.A. Paliichuk, and V.A. Shokol J. Org. Chem. USSR 20 1984 654 660
72. M.C. Elliott, and E. Williams Org. Biomol. Chem. 1 2003 3038 3047
73. L.E. Kaim, L. Grimaud, A. Lee, Y. Perroux, and C. Tirla Org. Lett. 6 2004 381 383
74. M. Aresta, C. Berloco, and E. Quaranta Tetrahedron 51 1995 8073 8088
75. J.W. Keillor, and X. Huang Org. Synth. 78 2000 234 238
76. L. Verotta, F. Orsini, M. Sbacchi, M.A. Scheildler, T.A. Amadorc, and E. Elisabetsky Bioorg. Med. Chem. 10 2002 2133 2142
77. 13C NMR spectra are in accord with Aldrich FT NMR, Vol. 3, 156B.
78. Compare S. Raucher, and D.S. Jones Synth. Commun. 15 1985 1025 1031
79. D.L. Boger, and R.S. Coleman J. Org. Chem. 49 1984 2240 2245