Synthesis of β-hydroxy dithiocarbamate derivatives via regioselective addition of dithiocarbamate anion to epoxide in water

Canadian Journal of Chemistry

Volumn 84, Issue 11, 2006, Pages 1515-1519

  Ziyaei Halimjani, Azim ^a   Saidi, Mohammad R ^a  

^a SHARIF UNIVERSITY OF TECHNOLOGY   (Iran)

Author keywords

Dithiocarbamate anion; Epoxide; Hydroxy dithiocarbamate; Water

Indexed keywords

DITHIOCARBAMATE ANION; HYDROXY DITHIOCARBAMATE;

DERIVATIVES; NEGATIVE IONS; SYNTHESIS (CHEMICAL); WATER;

ESTERS;

AMINE; BETA HYDROXY DITHIOCARBAMATE DERIVATIVE; CARBAMIC ACID DERIVATIVE; EPOXIDE; LITHIUM; PERCHLORATE; STYRENE OXIDE; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; ARTICLE; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; RNA TRANSLATION; SPECTROSCOPY; SYNTHESIS;

EID: 33846995620     PISSN: 00084042     EISSN: None     Source Type: Journal    
DOI: 10.1139/V06-150     Document Type: Article

References (41)

1. A.D. Dunn and W.D. Rudorf. Carbon disulfide in organic chemistry. Ellis Harwood, Chichester, UK. 1989. pp. 226-67.
2. C.H. Depuy and R.W. King. Chem. Rev. 60, 431 (1960).
3. (a) T.W. Greene and P.G.M. Wuts. Protective groups in organic synthesis. 3rd ed. Wiley-Interscience, New York. 1999. pp. 484-86;
4. (b) R.T.A. Mayadunne, E. Rizzardo, J. Chiefari, and Y.K. Chong. Macromalecules, 32, 6977 (1999).
5. B.H. Alexander, S.I. Gertler, T.A. Oda, R.T. Brown, R.W. Ihndris, and M. Beroza. J. Org. Chem. 25, 626 (1960).
6. G.D. Thorn and R.A. Ludwing. The Dithiocarbamates and related compounds. Elsevier, Amsterdam. 1962.
7. J.L. Serrano, L. Garcia, J. Perez, E. Perez, G. Sanchez, J. Garcia, G. Lopez, G. Garcia, and E. Molins. Inorg. Chim. Acta, 355, 33 (2003).
8. A. Ariafard, M.M. Amini, R. Fazaeli, and H.R. Aghabozorg. J. Mol. Struct. 636, 49 (2003).
9. B.W. Wenclawiak, S. Uttich, H. Deiseroth, and D. Schmitz. Inorg. Chim. Acta, 348, 1, (2003).
10. K.-H. Yih, G.-H. Lee, S.-L. Huang, and Y. Wang. J. Organomet. Chem. 665, 114 (2003).
11. A.W. M. Lee, W.H. Chan, H.C. Wang, and M.S. Wang. Synth. Commun. 19, 547 (1989).
12. I. Degani and R. Fochi. Synthesis, 365 (1978).
13. T.R. Burke, Jr., B.S. Bajwa, A.E. Jacobson, K.C. Rice, R.A. Streaty, and W.A. Klee. J. Med. Chem. 27, 1570 (1984).
14. W. Walter and K.D. Bode. Angew. Chem., Int. Ed. Engl. 6, 281 (1967).
15. (a) E. Lieber and R. Orlowski. J. Org. Chem. 22, 88 (1957);
16. (b) C.M. Buess. J. Am. Chem. Soc. 77, 6613 (1955).
17. (a) D.L. Fox, J.T. Ruxer, J.M. Oliver, K.L. Alford, and R.N. Salvatore. Tetrahedron Lett. 45, 401 (2004);
18. (b) R.N. Salvatore, J.A. Ledger, and K.W. Jung. Tetrahedron Lett. 42, 6023 (2001).
19. R.N. Salvatore, S. Sahab, and K.W. Jung. Tetrahedron Lett. 42, 2055 (2001).
20. R.N. Salvatore, S.I. Shin, A.S. Nagle, and K.W. Jung. J. Org. Chem. 66, 1035 (2001).
21. W. McGhee, D. Riley, K. Christ, Y. Pan, and B. Parnas. J. Org. Chem. 60, 2820 (1995).
22. (a) B. Guo, Z. Ge, T. Cheng, and R Li. Synth. Commun. 31, 3021 (2001);
23. (b) R.-T. Li, M.-S. Cai. Synth. Commun. 29, 65 (1999);
24. (c) Z. Ge, R. Li, and T. Cheng. Synth. Commun. 29, 3191 (1999).
25. N. Azizi, F. Aryanasab, L. Torkiyan, A. Ziyaei, and M.R. Saidi. J. Org. Chem. 71, 3634 (2006).
26. (a) P.A. Grieco (Editor). Organic synthesis in water. Blackie Academic and Professional, London. 1998;
27. (b) C.J. Li and T.H. Chang. In Organic reactions in aqueous media. Wiley, New York. 1997;
28. (c) S. Narayan, J. Muldoon, M.G. Finn, V.V. Fokin, H.C. Kolb, and K. B. Sharpless. Angew. Chem., Int. Ed. Engl. 44, 3275 (2005).
29. A. Ziyaei-Halimjani, and M.R. Saidi. Journal of Sulfur Chemistry, 26, 149 (2005).
30. (a) N. Azizi and M.R. Saidi. Org. Lett. 7, 3649 (2005);
31. (b) A. Ziyaei-Halimjani, N. Azizi, and M.R. Saidi. J. Mol. Catalysis A, 238, 138 (2005);
32. (c) A. Ziyaei-Halimjani, N. Azizi, and M.R. Saidi. J. Sci. I. R. Iran, 16, 37 (2005);
33. (d) F. Rajabi and M.R. Saidi. Synth. Commun. 35, 483 (2005);
34. (e) N. Azizi and M.R. Saidi. Can. J. Chem. 83, 505 (2005);
35. (f) F. Rajabi and M.R. Saidi. Synth. Commun. 34, 4179 (2004).
36. (g) N. Azizi and M.R. Saidi. Synth. Commun. 34, 1207 (2004);
37. (h) N. Azizi and M.R. Saidi. Organometallics, 23, 1457 (2004);
38. (i) N. Azizi and M.R. Saidi. Tetrahedron, 60, 383 (2004);
39. (j) N. Azizi, F. Rajabi, and M.R. Saidi. Tetrahedron Lett. 45, 9233 (2004);
40. (k) N. Azizi and M.R. Saidi. Eur. J. Org. Chem. 4630 (2003).
41. (l) N. Azizi and M.R. Saidi. J. Organomet. Chem. 688, 283 (2003).