Trimethylsilyl chloride promoted selective desulfurization of thiocarbonyls to carbonyls with hydrogen peroxide

Synthesis

Volumn , Issue 24, 2010, Pages 4282-4286

  Bahrami, Kiumars ^a   Khodaei, Mohammad Mehdi ^a   Tajik, Maryam ^a  

^a RAZI UNIVERSITY   (Iran)

Author keywords

desulfurization; hydrogen peroxide; protecting groups; thiocarbonyls; trimethylsilyl chloride

Indexed keywords

ENVIRONMENTALLY BENIGN; PROTECTING GROUP; SHORT REACTION TIME; SIDE REACTIONS; THIOCARBONYLS; TRIMETHYLSILYL CHLORIDE;

CARBONYLATION; CHLORINE COMPOUNDS; DESULFURIZATION; HYDROGEN; OXIDATION;

HYDROGEN PEROXIDE;

CARBONYL DERIVATIVE; CHLOROTRIMETHYLSILANE; HYDROGEN PEROXIDE; LEWIS ACID; THIOBENZAMIDE DERIVATIVE;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; DESULFURIZATION; ELECTROPHILICITY; NUCLEOPHILICITY; OXIDATION; REACTION OPTIMIZATION; REACTION TIME;

EID: 78650179892     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0030-1258283     Document Type: Article

References (69)

1. Hanessian S, Reddy G J., Chahal N, Org. Lett. 2006 8 5477
2. Jones S B., He L, Castle S L., Org. Lett. 2006 8 3757
3. Va P, Roush W R., J. Am. Chem. Soc. 2006 128 15960
4. Fuwa H, Ebine M, Bourdelais A J., Baden D G., Sasaki M, J. Am. Chem. Soc. 2006 128 16989
5. Rani R, Rahmanana M F., Bhalerao U T., Tetrahedron 1992 48 1953
6. Dhar D N., Bag A K., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985 24 445
7. Kristensen R B., Thomsen I, Lawesson S.-O, Sulfur Lett. 1985 3 7
8. Jorgensen K A., Ghattas A.-B A. G., Lawesson S.-O, Tetrahedron 1982 38 1163
9. Kim Y H., Chung B C., Chang H S., Tetrahedron Lett. 1985 26 1079
10. Varma R S., Kumar D, Synth. Commun. 1999 29 1333
11. Movassagh B, Lakouraj M M., Ghodrati K, Synth. Commun. 2000 30 2353
12. Mohammadpoor-Baltork I, Khodaei M M., Nikoofar K, Tetrahedron Lett. 2003 44 591
13. Mohammadpoor-Baltork I, Memarian H R., Hajipour A R., Bahrami K, Bull. Korean Chem. Soc. 2003 24 1002
14. Tamagaki S, Hatanaka I, Kozuka S, Bull. Chem. Soc. Jpn. 1977 50 3421
15. Ley S V., Meerholz C A., Barton D H. R., Tetrahedron Lett. 1980 21 1785
16. Cussans N J., Ley S V., Barton D H. R., J. Chem. Soc., Perkin Trans. 1 1980 1650
17. Abuzar S, Sharma S, Iyer R N., Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1980 19 211
18. Kochhar K S., Cottrell D A., Pinnick H W., Tetrahedron Lett. 1983 24 1323
19. Tabüchi T, Nojima M, Kusabayashi S, J. Chem. Soc., Perkin Trans. 1 1991 3043
20. Tabüchi T, Nojima M, Kusabayashi S, J. Chem. Soc., Chem. Commun. 1990 625
21. Ellis J, Frier R D., Schibeci R A., Aust. J. Chem. 1971 24 1527
22. Hall J, Satchell D P. N., J. Chem. Soc., Perkin Trans. 2 1975 1351
23. Micallef J V., Satchell D P. N., J. Chem. Soc., Perkin Trans. 2 1982 971
24. Micallef J V., Satchell D P. N., J. Chem. Soc., Perkin Trans. 2 1982 1379
25. Chalais S, Cornelis A, Laszlo P, Mathy A, Tetrahedron Lett. 1985 26 2327
26. Narasimhamurthy N, Samuelson A G., Tetrahedron Lett. 1986 27 3911
27. Yoshihiro Y, Matsumoto N, Hamasaki R, Tanabe Y, Tetrahedron Lett. 1999 40 4227
28. Sabitha G, Reddy G S. K. K., Reddy C S., Yadav J S., Synlett 2003 858
29. Dabkowski W, Tworowska I, Michalski J, Cramer F, Chem. Commun. 1997 877
30. Prakash G K. S., Mathew T, Panja C, Olah G A., J. Org. Chem. 2007 72 5847
31. Ryabukhin S V., Plaskon A S., Ostapchuk E N., Volochnyuk D M., Tolmachev A A., Synthesis 2007 417
32. Ryabukhin S V., Plaskon A S., Volochnyuk D M., Tolmachev A A., Synthesis 2006 3715
33. Corey E J., Boaz N W., Tetrahedron Lett. 1985 26 6015
34. Bertz S H., Miao G, Rossiter B E., Snyder J P., J. Am. Chem. Soc. 1995 117 11023
35. Terang N, Mehta B K., Ila H, Junijappa H, Tetrahedron 1998 54 12973
36. Iwai T, Ito T, Mizumo T, Ishino Y, Tetrahedron Lett. 2004 45 1083
37. Kobayashi K, Takanohashi A, Hashimoto K, Morikawa O, Konishi H, Tetrahedron 2006 62 3158
38. Chen Y.-J, Huang Y.-P, Tetrahedron Lett. 2000 41 5233
39. Yamanaka M, Nishida A, Nakagawa M, J. Org. Chem. 2003 68 3112
40. Sakai N, Hirasawa M, Hamajima T, Konakahara T, J. Org. Chem. 2003 68 483
41. Jiang B, Si Y G., Tetrahedron Lett. 2003 44 6767
42. Ishino Y, Mihara M, Takeuchi T, Takemoto M, Tetrahedron Lett. 2004 45 3503
43. Ryabukhin S V., Plaskon A S., Volochnyuk D M., Tolmachev A A., Synlett 2004 2287
44. Yoshikawa E, Gevorgyan V, Asao N, Yamamoto Y, J. Am. Chem. Soc. 1997 119 6781
45. Bahrami K, Tetrahedron Lett. 2006 47 2009
46. Khodaei M M., Bahrami K, Khedri M, Can. J. Chem. 2007 85 7
47. Bahrami K, Khodaei M M., Kavianinia I, Synthesis 2007 547
48. Khodaei M M., Bahrami K, Karimi A, Synthesis 2008 1682
49. Bahrami K, Khodaei M M., Naali F, J. Org. Chem. 2008 73 6835
50. Bahrami K, Khodaei M M., Naali F, Synlett 2009 569
51. Khodaei M M., Bahrami K, Tirandaz Y, J. Sulfur Chem. 2009 30 581
52. Bahrami K, Khodaei M M., Soheilizad M, Synlett 2009 2773
53. Bahrami K, Khodaei M M., Soheilizad M, J. Org. Chem. 2009 74 9287
54. Bahrami K, Khodaei M M., Farrokhi A, Tetrahedron 2009 65 7658
55. Bahrami K, Khodaei M M., Tirandaz Y, Synthesis 2009 369
56. Mohammadpoor-Baltork I, Memarian H R., Bahrami K, Monatsh. Chem. 2004 135 411
57. Elson K E., Jenkinsb I D., Loughlin W A., Tetrahedron Lett. 2004 45 2491
58. Al-Awadi H, Ibrahim M R., Dib H H., Al-Awadi N A., Ibrahim Y A., Tetrahedron 2005 61 10507
59. Rahman A.-U, Basha A, Waheed N, Tetrahedron Lett. 1976 17 219
60. Gajda T, Zwierzak I, Synthesis 1981 1005
61. Olah C A., Arvanaghi M, Ohannesian L, Surya P G. K., Synthesis 1984 785
62. Dictionary of Organic Compounds 5th ed., Vol. 1 Buckingham J Chapman and Hall London 1982 19
63. Lajis N, Pertanika 1985 8 67
64. Masuda R, Hojo M, Ichi T, Sasano S, Kobayashi T, Kuroda C, Tetrahedron Lett. 1991 32 1195
65. Ho T L., Synth. Commun. 1979 9 37
66. Scheeren J W., Ooms P H. J., Nivard R J. F., Synthesis 1973 149
67. Fieser L F., Fieser M, Reagents for Organic Synthesis Vol. 1 Wiley New York 1967 333
68. Pedersen B S., Scheibye S, Nilsson N H., Lawesson S.-O, Bull. Soc. Chim. Belg. 1978 87 223
69. Pedersen B S., Scheibye S, Clausen K, Lawesson S.-O, Bull. Soc. Chim. Belg. 1978 87 293