One-pot, three-step preparation of alkyl and aryl alkylcarbamates from S-methyl N-alkylthiocarbamates

Synthesis

Volumn , Issue 10, 2008, Pages 1612-1618

  Artuso, Emma ^a   Degani, Iacopo ^a   Fochi, Rita ^a   Magistris, Claudio ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

Amines; Carbamates; Dithiocarbonates; Isocyanates; Thiocarbamates

Indexed keywords

CHLORINE COMPOUNDS; COBALT; COBALT COMPOUNDS;

AVERAGE YIELD; DIMETHYL DISULFIDE (DMDS); GENERAL (CO); INDUSTRIAL INTEREST; ONE POT; SYNTHESIS (OF CHIRAL IONIC LIQUIDS); THIOCARBAMATE;

ALKYLATION;

ALKYL GROUP; CARBAMIC ACID; CARBAMOYL CHLORIDE; DIMETHYL DISULFIDE; ISOCYANATE; METHYLTHIOCARBAMATE; REAGENT; THIOCARBAMIC ACID DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; ONE POT SYNTHESIS; SYNTHESIS;

EID: 44949263868     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1072573     Document Type: Article

References (63)

1. Artuso, E.; Degani, I.; Fochi, R.; Magistris, C. Synthesis 2007, 3497.
2. Artuso, E.; Carvoli, G.; Degani, I.; Fochi, R.; Magistris, C. Synthesis 2007, 1096.
3. (a) Carvoli, G.; Degani, I.; Pallucca, E.; Fochi, R.; Gazzetto, S.; Artuso, E.; Lazzaroni, M.; Cadamuro, S. Oxon Italia S.p.A., Italy, patent request No. MI 2005 001284, 2005.
4. (b) Carvoli, G.; Degani, I.; Pallucca, E.; Fochi, R.; Serri, A. M.; Cadamuro, S.; Gazzetto, S.; Migliaccio, M. Oxon Italia S.p.A., Italy, patent request No. MI 2004 002402, 2004.
5. For reviews on carbamates, see: (a) Chaturvedi, D.; Ray, S. Chem. Rev. 2006, 137, 127.
6. (b) Rossi, L. In Science of Synthesis, Vol. 18; Knight, J. G., Ed.; Thieme Verlag: Stuttgart, 2005, 461-598.
7. (c) Belli Dell'Amico, D.; Calderazzo, F.; Labella, L.; Marchetti, F.; Pampaloni, G. Chem. Rev. 2003, 103, 3857.
8. (d) Petersen, U. In Houben-Weyl, 4th ed., Vol. E4; Hagemann, H., Ed.; Thieme: Stuttgart, 1983, 142-238.
9. (e) Melnikov, N. N. In Chemistry of Pesticides; Gunther, F. A.; Gunther, J. D., Eds.; Springer-Verlag: Berlin, 1971, 206-222.
10. (f) Adams, P.; Baron, F. A. Chem. Rev. 1965, 65, 567.
11. For plentiful literature on the syntheses and applications of carbamates, see: Feroci, M.; Casadei, M. A.; Palombi, L.; Inesi, A. J. Org. Chem. 2003, 68, 1548; and references cited therein.
12. For plentiful literature on the syntheses of carbamates using carbon dioxide, see: Feroci, M.; Orsini, M.; Sotgiu, G.; Rossi, L.; Inesi, A. J. Org. Chem. 2007, 72, 200; and references cited therein.
13. For example, for toxicity of phosgene, see: (a) Cotarca, L.; Eckert, H. In Phosgenations - A Handbook; Wiley-VCH: Weinheim, 2003, 9.
14. (b) Senet, J.-P.(Groups SNPE) In The Recent Advance in Phosgene Chemistry, Vol. 1; GPA: Nanterre, 1997, 10-11.
15. (c) Sax, N. I. In Dangerous Properties of Industrial Materials; Van Nostrand Reinhold Company: New York, 1984, 2210-2211.
16. For some recent references on carbamates (after 2005), see: (a) Gogoi, P.; Konwar, D. Tetrahedron Lett. 2007, 48, 531.
17. (b) Singh, O. V.; Han, H. J. Am. Chem. Soc. 2007, 129, 774.
18. (c) Meudt, A.; Böhm, C.; Schweitzer, K. Archimica GmbH Germany, WO 2007006465, 2007; Chem. Abstr. 2007, 146, 162924.
19. (d) Singh, K. N. Synth. Commun. 2007, 37, 2651.
20. (e) Srinivas, D.; Srivastava, R.; Ratnasamy, P. US 20070270605, 2007; Chem. Abstr. 2007, 148, 12984.
21. (f) Han, C.; Porco, J. A. Org. Lett. 2007, 9, 1517.
22. (g) Zheng, S.; Li, F.; Liu, J.; Xia, C. Tetrahedron Lett. 2007, 48, 5883.
23. (h) Orito, K.; Miyazawa, M.; Nakamura, T.; Horibata, A.; Ushito, H.; Nagasaki, H.; Yuguchi, M.; Yamashita, S.; Yamazaki, T.; Tokuda, M. J. Org. Chem. 2006, 71, 5951.
24. (i) Distaso, M.; Quaranta, E. Appl. Catal. B 2006, 66, 72.
25. (j) Litwnowicz, M.; Kijenski, J.; Kwiatkowski, J.; Pasinska-Grochowy, D. Przem. Chem. 2006, 85, 114;
26. Chem. Abstr. 2006, 145, 358699.
27. (k) Gupte, S. P.; Chaudari, R. V.; Anandkumar, B. S.; Mulla, S. A. Council of Scientific & Industrial Research India, WO 2005063698, 2005; Chem. Abstr. 2005, 143, 77708.
28. (l) Gupte, S. P.; Chaudari, R. V.; Anandkumar, B. S.; Mulla, S. A. Council of Scientific & Industrial Research India, US 2005222450, 2005; Chem. Abstr. 2005, 143, 115358.
29. (m) Srivastava, R.; Srinivas, D.; Ratnasamy, P. Appl. Catal. 2005, 289, 128.
30. (n) Chaturvedi, D.; Ray, S. Lett. Org. Chem. 2005, 2, 742;
31. Chem. Abstr. 2006, 144, 488108.
32. (o) Lebel, H.; Leogane, O. Org. Lett. 2005, 7, 4107.
33. (p) Hiegel, G. A.; Hogenauer, T. J. Synth. Commun. 2005, 35, 2091.
34. (q) Spino, C.; Joly, M.-A.; Godbout, C.; Arbour, M. J. Org. Chem. 2005, 70, 6118.
35. (r) Grzyb, J. A.; Shen, M.; Yoshina-Ishii, C.; Chi, W.; Brown, R. S. Tetrahedron 2005, 61, 7153.
36. (s) Ramesh, R.; Bhat, R. G.; Chandrasekaran, S. J. Org. Chem. 2005, 70, 837.
37. (t) Raje, V. P.; Bhat, R. P.; Samant, S. D. Tetrahedron. Lett. 2005, 46, 835.
38. Minato, H.; Takeda, K.; Miura, T.; Kobayashi, M. Chem. Lett. 1977, 1095.
39. (a) Cotarca, L.; Eckert, H. In Phosgenations - A Handbook; Wiley-VCH: Weinheim, 2003, 208-210 and 270-273.
40. (b) Bigi, F.; Sartori, G. Green Chem. 2000, 2, 140.
41. Oxon Italia S.p.A., 20016 Pero (Milano), Italy.
42. Degani, I.; Fochi, R.; Regondi, V. Synthesis 1981, 149.
43. D'Silva, T. D. J.; Lopes, A.; Jones, R. L.; Singhawangcha, S.; Chan, J. K. J. Org. Chem. 1986, 51, 3781.
44. Dictionary of Organic Compounds on CD-ROM; Chapman & Hall, Electronic Publishing Division: London, 2007, Version 15.2 [CD ROM].
45. Spectral Data Base for Organic Compounds SDBS (National Institute of Advanced Industrial Science and Technology). SDBS Web: http://riodb.ibase.aist. go.jp/index.html.
46. Details are reported in reference 4a.
47. ( 18) Kolbezen, M. J.; Metcalf, R. L.; Fukuto, T. R. J. Agric Food Chem. 1954, 2, 864.
48. Heiss, R.; Bocker, E.; Morschel, H. Bayer AG, DE 1165577, 1964; Chem. Abstr. 1964, 61, 1797a.
49. Al-Rawi, H.; Williams, A. J. Am. Chem. Soc. 1977, 99, 2671.
50. Pianka, M.; Polton, D. J. J. Chem. Soc. 1960, 983.
51. Yu, Q. S.; Schoenenberger, B.; Brossi, A. Heterocycles 1987, 26, 1271.
52. Wallace, G. C.; Zerba, E. N. Pestic. Sci. 1989, 215.
53. Ben-Ishai, D.; Katchalski, E. J. Org. Chem. 1951, 16, 1025.
54. Pelah, Z. Makhteshim Chem Works LTD, DE 1910296, 1969; Chem. Abstr. 1970, 72, 43298e.
55. Berntsson, P.; Brandstrom, A.; Junggren, U.; Palmer, L.; Sjostrandi, S. E.; Sundell, G. Acta Pharm. Suec. 1977, 14, 229;
56. Chem. Abstr. 1978, 89, 59754.
57. Schalk, W.; Schmied-Kowarzik, V. Union Carbide Corp., DE 1138277, 1960; Chem. Abstr. 1961, 55, 2591b.
58. Ramesh, R.; Chandrasekaran, Y.; Legha, R.; Chandrasekaran, S. Tetrahedron 2007, 63, 9153.
59. Pierce, A. C.; Joullie, M. M. J. Org. Chem. 1963, 28, 658.
60. McGhee, W.; Riley, D.; Christ, K.; Pan, Y.; Parnas, B. J. Org. Chem. 1995, 60, 2820.
61. Fraley, R. W. PPG Industries Inc., US 3734945, 1971; Chem. Abstr. 1971, 79, 18453.
62. Patonay, T.; Patonay-Peli, E.; Mogyorodi, F. Synth. Commun. 1990, 20, 2865.
63. Thompson, R. D.; Baumgarten, H. E. Org. Synth. Coll. Vol. V; John Wiley & Sons: London, 1973, 709.