Microwave thermolysis I: A convenient and rapid coupling of thiols using 'Clayan' in solvent free condition

Synthetic Communications

Volumn 30, Issue 4, 2000, Pages 701-706

  Meshram, H M ^a   Bandyopadhyay, A ^a   Reddy, G S ^a   Yadav, J S ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

DISULFIDE; THIOL DERIVATIVE;

ARTICLE; MICROWAVE RADIATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0033964275     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008087372     Document Type: Article

References (41)

1. a) Fontana, S.A.; Davis, C.R.; He, Y.B. and Burton, D.J. Tetrahedron Lett. 1996, 52, 27.
2. b) Ogawa, A.; Nishiyama, T.; Kambe, N., Murai, S. and Sonada, N. Tetrahedron Lett. 1987, 28, 3271.
3. Johnson, J.R.; Bruce, W.F. and Dutcher, J.D. J. Am. Chem. Soc 1943, 65, 2005.; Miller, P.A.; Milstrey, K.P.; and Trown, P.W. Science, 1968, 159, 431
4. Johnson, J.R.; Bruce, W.F. and Dutcher, J.D. J. Am. Chem. Soc 1943, 65, 2005.; Miller, P.A.; Milstrey, K.P.; and Trown, P.W. Science, 1968, 159, 431
5. Bodanszky, M. "Principle of Peptide Synthesis", Springer-Verlag, Berlin, 1984, chapter 4.
6. Kitamura, T.; Nutsyuki, J. and Taniguch, H. J. Chem. Soc. Perkin Trans. 1. 1991, 1601.
7. a) Sato, T.; Otera, J. and Nozaki, H. Tetrahedron Lett. 1990, 31, 3591.; Wallace, T.J. J. Org. Chem 1966, 31, 3071.; Drabowicz, J. and Mikolajezyk, M. Synthesis. 1980, 32.; McKillop, A. and Koyunou, D. Tetrahedron Lett. 1990, 31, 5007.
8. a) Sato, T.; Otera, J. and Nozaki, H. Tetrahedron Lett. 1990, 31, 3591.; Wallace, T.J. J. Org. Chem 1966, 31, 3071.; Drabowicz, J. and Mikolajezyk, M. Synthesis. 1980, 32.; McKillop, A. and Koyunou, D. Tetrahedron Lett. 1990, 31, 5007.
9. a) Sato, T.; Otera, J. and Nozaki, H. Tetrahedron Lett. 1990, 31, 3591.; Wallace, T.J. J. Org. Chem 1966, 31, 3071.; Drabowicz, J. and Mikolajezyk, M. Synthesis. 1980, 32.; McKillop, A. and Koyunou, D. Tetrahedron Lett. 1990, 31, 5007.
10. a) Sato, T.; Otera, J. and Nozaki, H. Tetrahedron Lett. 1990, 31, 3591.; Wallace, T.J. J. Org. Chem 1966, 31, 3071.; Drabowicz, J. and Mikolajezyk, M. Synthesis. 1980, 32.; McKillop, A. and Koyunou, D. Tetrahedron Lett. 1990, 31, 5007.
11. b) Fristad, E. and Peterson, R. Synth. Commun. 1985, 15, 1.
12. c) Firouzabadi, H.; Iranpoor, N.; Pathare, H.; Sardarian, A. and Toofan, J. Synth. Commun. 1984, 14, 717
13. d) Meshram, H.M. Org. Prep. Procd. Int. 1993, 25, 232.
14. e) Huang, Y.; Zhang, Y. and Wang, Y. Synth. Commun 1997, 27, 1043.
15. f) Kurana, J.M.; Singh, S. and Sehgal, A. Indian J. Chem. 1997, 368, 819.
16. g) Hirano, M., Yakabe, S.; Fukami, M. and Morinofo, T. Synth. Commun. 1997, 27, 2783.
17. a) Firouzabadi, H.; Iranpoor, N.; Zolfigol, M.A. Synth. Commun 1998, 28, 1179.
18. b) Iranpoor, N.; Firouzabadi, H. Synth. Commun. 1998, 28, 367.
19. Drabowicz, J. and Mikolajezyk, M Synthesis. 1980, 32.
20. Tam, J.P.; Wu, C.R.; Liu, W. and Zhang, J.W. J. Am. Chem. Soc. 1991, 113, 6657.
21. a) Illman, D.L. Chem. and Engg. News. 1994, Sept. 5, 22.
22. b) Cusumano, J. A. J. Chem Educ., 1995, 72, 959
23. c) Hartman, I.S. and Soltzberg, L.J. J. Chem. Educ., 1995, 72, 981.
24. d) Horvath, I.T. Chem. Rev., 1995, 95, 1.
25. a) Abramovitch, R.A. Org. Prep. Procd. Int. 1991, 23, 683.
26. b) Caddick, S. Tetrahedron. 1995, 51, 10403
27. a) Varma, R.S. and Meshram, H.H. Tetrahedron Lett. 1997, 38, 5427.
28. b) Varma, R.S.; Saini, R.K. and Meshram, H.M. Tetrahedron Lett. 1997, 38, 6525.
29. Haggin, J. Chem. and Engg. News. 1994, April 18, 22.
30. a) Meshram, H.M. Tetrahedron Lett. 1993, 34, 2541.
31. b) Meshram, H.M.; Reddy, G.S. and Yadav, J.S. Tetrahedron Lett. 1997, 38, 8891.
32. c) Meshram, H.M.; Srinivas, D. and Yadav, J.S. Tetrahedron Lett. 1997, 38, 8743.
33. d) Meshram, H.M.; Reddy, G.S.; Srinivas, D. and Yadav, J.S. Synth. Commun. 1998, 28, 2593.
34. a) Meshram, H.M.; Srinivas, D., Reddy, G.S. and Yadav, J.S. Synth. Commun., 1998, 28, 4401.
35. b) Yadav, J.S., Meshram, H.M.; Reddy, G.S. and Sumithra, G. Tetrahedron Lett. 1998, 39, 3043.
36. After irradiation of the reaction mixture (thiophenol : reagent 1:3) for 30 seconds inside a BPL microwave oven at full power (800 W), the temperature of the alumina bath was found to be 65 °C Similar yield of the disulphide is obtained using alternate mode of heating (conventional oil bath at 65 °C, 3 h )
37. For a critical evaluation and activation processes by microwaves see: a) Whittaker, A. G.; Mingos, D. M. P. J. Microwave Power Eletromagn. Energy. 1994, 29, 195.
38. b) Majetich, G., Hicks, R. J. Microwave Power Eletromagn. Energy. 1995, 30, 27.
39. Laszlo, P. and Carnelis, A. Aldrichimica Acta 1988, 21, 97.
40. E.E. Reid, "Organic Chemistry of Bivalent Sulfur Compounds", Chemical Publishing Co., Inc. 1960, vol. III.
41. Danehy, J.P.; Elia, V.J. and Lavelle, C.J. J. Org. Chem 1971, 36, 1003.