Ionic liquid/PPh 3 promoted cleavage of diphenyl disulfide and diselenide: A straight-forward metal-free one-pot route to the synthesis of unsymmetrical sulfides and selenides

Tetrahedron Letters

Volumn 53, Issue 17, 2012, Pages 2149-2152

  Banerjee, Subhash ^a   Adak, Laksmikanta ^a   Ranu, Brindaban C ^a  

^a DEPARTMENT OF MATERIALS SCIENCE   (India)

Author keywords

1,4 Addition; Green synthesis; Ionic liquid; Sulfides and selenides; Triphenyl phosphine

Indexed keywords

1 METHYL 3 PENTYLIMIDAZOLIUM BROMIDE; ALKENE; DIPHENYL DISULFIDE; DISELENIDE; DISULFIDE; HALIDE; IONIC LIQUID; PHOSPHINE DERIVATIVE; SELENIDE; SOLVENT; TRIPHENYL PHOSPHINE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; GREEN CHEMISTRY; INFRARED SPECTROSCOPY; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

EID: 84858700221     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2012.02.047     Document Type: Article

References (53)

1. M.D. McReynolds, J.M. Doughtery, and P.R. Hanson Chem. Rev. 104 2004 2239 2258
2. R.J. Cremlyn An Introduction to Organosulfur Chemistry 1996 Wiley New York pp 1-262
3. S. Oae, and T. Okuyama Organic Sulfur Chemistry Biochemical Aspects; 1992 CRC Press Boca Raton pp 1-260
4. A. Krief, and L. Hevesi Organoselenium Chemistry Vol. 1 1988 Springer Berlin
5. A. Krief B.M. Trost, Comprehensive Organometallic Chemistry 1991 Pergamon Press Oxford 85 192
6. J. Ham, I. Yang, and H.H. Kang J. Org. Chem 69 2004 3236 3239 and references cited therein
7. P.S. Herradura, K.A. Pendola, and R.K. Guy Org. Lett. 2 2000 2019 2022
8. C. Goux, P. Lhoste, and D. Sinou Tetrahedron Lett. 33 1992 8099 8102
9. T. Kondo, and T. Mitsudo Chem. Rev. 100 2000 3205 3220
10. S.V. Ley, and A.W. Thomas Angew. Chem., Int. Ed. 42 2003 5400 5449
11. N. Taniguchi J. Org. Chem. 69 2004 6904 6906
12. Y. Guindon, R. Frenette, R. Fortin, and J. Rokach J. Org. Chem. 48 1983 1357 1359
13. M.T. Martin, A.M. Thomas, and D.G. York Tetrahedron Lett 43 2002 2145 2147 and references cited therein
14. P. Perlmutter Conjugated Addition Reaction in Organic Synthesis 1992 Oxford Pergamon pp 1-394
15. B.C. Ranu, S. Bhar, and D.C. Sarkar Tetrahedron Lett. 32 1991 2811 2812
16. N. Srivastava, and B.K. Banik J. Org. Chem. 68 2003 2109 2114
17. R. Sreekumar, P. Rugmimi, and R. Padmakumar Tetrahedron Lett. 38 1997 6557 6560
18. S. Sebti, A. Saber, and A. Rhihil Tetrahedron Lett. 35 1994 9399 9400
19. M.M. Alam, R. Varala, and S.R. Adapa Tetrahedron Lett. 44 2003 5115 5119
20. S. Cheng, and D.D. Comer Tetrahedron Lett. 43 2002 1179 1181
21. M. Bandini, P.G. Cozzi, M. Giacomoni, P. Melchiorre, S. Selva, and A.U. Ronchi J. Org. Chem. 67 2002 3700 3704
22. M. Zahouily, Y. Abrouki, A. Rayadh, S. Sebti, H. Dhimane, and M. David Tetrahedron Lett 44 2003 2463 2465 and references cited therein
23. B.C. Ranu, S.S. Dey, and A. Hajra Tetrahedron 59 2003 2417 2421
24. J.S. Yadav, B.V.S. Reddy, and G. Baishya J. Org. Chem. 68 2003 7098 7100
25. B.C. Ranu, and S.S. Dey Tetrahedron 60 2004 4183 4188
26. B. Movassagh, and M. Shamsipoor Synlett 2005 121 122
27. C. Mukherjee, P. Tiwari, and A.K. Misra Tetrahedron Lett. 47 2006 441 445
28. L.W. Bieber, A.C.P.F. Sa, P.H. Menezes, and S.M.C. Goncalves Tetrahedron Lett. 42 2001 4597 4599
29. X. Zhao, Z. Yu, S. Yan, S. Wu, R. Liu, W. He, and L. Wang J. Org. Chem. 70 2005 7338 7341
30. T. Nishino, M. Okada, T. Kuroki, T. Watanabe, Y. Nishiyama, and N. Sonoda J. Org. Chem. 67 2002 8696 8698
31. B.C. Ranu, T. Mandal, and S. Samanta Org. Lett. 5 2003 1439 1441
32. B.C. Ranu, and T. Mandal J. Org. Chem. 69 2004 5793 5795
33. B.C. Ranu, and T. Mandal Synlett 2004 1239 1242
34. W. Duane Brown Biochim. Biophys. Acta 44 1960 365
35. L.E. Overman, J. Smoot, and J.D. Overman Synthesis 1974 59 60
36. A. Schonberg, and M.Z. Barakat J. Chem. Soc. 1949 892
37. L.E. Overman, D. Matzinger, E.M.O. Connor, and J.D. Overman J. Am. Chem. Soc. 96 1974 6081 6089
38. T. Welton Chem. Rev. 99 1999 2071 2084
39. V.I. Parvulescu, and C. Hardacre Chem. Rev. 107 2007 2615 2665
40. J.A. Boon, J.A. Levinsky, J.I. Pflug, and J.S. Wilkes J. Org. Chem. 51 1986 480 483
41. J.R. Harjani, S.J. Nara, and M.M. Salunkhe Tetrahedron Lett. 43 2002 1127 1130
42. V.V. Namboodiri, and R.S. Varma Chem. Commun. 2002 342 343
43. W. Sun, C.-G. Xia, and H.-W. Wang Tetrahedron Lett. 44 2003 2409 2411
44. K. Qiao, and C. Yakoyama Chem. Lett. 33 2004 472 473
45. B.C. Ranu, and S. Banerjee Org. Lett. 7 2005 3049 3052
46. B.C. Ranu, A. Saha, and S. Banerjee Eur. J. Org. Chem. 2008 519 523
47. B.C. Ranu, L. Adak, and S. Banerjee Tetrahedron Lett. 49 2008 4613 4617
48. T. Cohen, and B.-S. Guo Tetrahedron 42 1986 2803 2808
49. K.-I. Ikeshita, N. Kihara, and A. Ogawa Tetrahedron Lett. 46 2005 8773 8775
50. J. Wang, H. Li, Y. Mei, B. Lou, D. Xu, D. Xie, H. Guo, and W. Wang J. Org. Chem. 70 2005 5678 5687
51. O.A. Wallner, and K.J. Szabo J. Org. Chem. 70 2005 9215 9221
52. V.A.C. Valeria, B. Fernando, D.C. Antonella, M. Luigi, R. Ivan, and S. Luca J. Org. Chem. 64 1999 8122 8126
53. This ionic liquid was prepared by the reaction of N-methylimidazole and pentyl bromide following a reported procedure (Namboodiri, V. V.; Varma, R. S. Org. Lett. 2002, 4, 3161-3163).