Trimethylsilyl Chloride Promoted
Selective Desulfurization of Thiocarbonyls to Carbonyls with Hydrogen
Peroxide

Kiumars Bahrami; Mohammad Mehdi Khodaei; Maryam Tajik

doi:10.1055/s-0030-1258283

PAPER

Trimethylsilyl Chloride Promoted Selective Desulfurization of Thiocarbonyls to Carbonyls with Hydrogen Peroxide

Kiumars Bahrami*^a,b, Mohammad Mehdi Khodaei*^a,b, Maryam Tajik^a
^a Department of Chemistry, Razi University, Kermanshah 67149-67346, Iran
Fax: +98(831)4274559; e-Mail: kbahrami2@hotmail.com; e-Mail: mmkhoda@razi.ac.ir;
^b Nanoscience and Nanotechnology Research Center (NNRC), Razi University, Kermanshah 67149-67346, Iran

Abstract

Alle Artikel dieser Rubrik

Abstract

In the presence of hydrogen peroxide and trimethylsilyl chloride, thiocarbonyls desulfurize to the corresponding carbonyls. The safe, operationally simple, general reaction gives excellent yields in short reaction times with no side reactions and excellent regioselectivity, which makes this process an attractive, environmentally benign alternative for the desulfurization of thiocarbonyls.

Key words

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

Volltext

Referenzen

References

1a Hanessian S. Reddy GJ. Chahal N. Org. Lett. 2006, 8: 5477

1b Jones SB. He L. Castle SL. Org. Lett. 2006, 8: 3757

1c Va P. Roush WR. J. Am. Chem. Soc. 2006, 128: 15960

1d Fuwa H. Ebine M. Bourdelais AJ. Baden DG. Sasaki M. J. Am. Chem. Soc. 2006, 128: 16989

2a Rani R. Rahmanana MF. Bhalerao UT. Tetrahedron 1992, 48: 1953

2b Dhar DN. Bag AK. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24: 445

2c Kristensen RB. Thomsen I. Lawesson S.-O. Sulfur Lett. 1985, 3: 7

2d Jorgensen KA. Ghattas A.-BAG. Lawesson S.-O. Tetrahedron 1982, 38: 1163

2e Kim YH. Chung BC. Chang HS. Tetrahedron Lett. 1985, 26: 1079

2f Varma RS. Kumar D. Synth. Commun. 1999, 29: 1333

2g Movassagh B. Lakouraj MM. Ghodrati K. Synth. Commun. 2000, 30: 2353

2h Mohammadpoor-Baltork I. Khodaei MM. Nikoofar K. Tetrahedron Lett. 2003, 44: 591

2i Mohammadpoor-Baltork I. Memarian HR. Hajipour AR. Bahrami K. Bull. Korean Chem. Soc. 2003, 24: 1002

3a Tamagaki S. Hatanaka I. Kozuka S. Bull. Chem. Soc. Jpn. 1977, 50: 3421

3b Ley SV. Meerholz CA. Barton DHR. Tetrahedron Lett. 1980, 21: 1785

3c Cussans NJ. Ley SV. Barton DHR. J. Chem. Soc., Perkin Trans. 1 1980, 1650

3d Abuzar S. Sharma S. Iyer RN. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1980, 19: 211

3e Kochhar KS. Cottrell DA. Pinnick HW. Tetrahedron Lett. 1983, 24: 1323

3f Tabüchi T. Nojima M. Kusabayashi S. J. Chem. Soc., Perkin Trans. 1 1991, 3043

3g Tabüchi T. Nojima M. Kusabayashi S. J. Chem. Soc., Chem. Commun. 1990, 625

4a Ellis J. Frier RD. Schibeci RA. Aust. J. Chem. 1971, 24: 1527

4b Hall J. Satchell DPN. J. Chem. Soc., Perkin Trans. 2 1975, 1351

4c Micallef JV. Satchell DPN. J. Chem. Soc., Perkin Trans. 2 1982, 971

4d Micallef JV. Satchell DPN. J. Chem. Soc., Perkin Trans. 2 1982, 1379

4e Chalais S. Cornelis A. Laszlo P. Mathy A. Tetrahedron Lett. 1985, 26: 2327

4f Narasimhamurthy N. Samuelson AG. Tetrahedron Lett. 1986, 27: 3911

5a Yoshihiro Y. Matsumoto N. Hamasaki R. Tanabe Y. Tetrahedron Lett. 1999, 40: 4227

5b Sabitha G. Reddy GSKK. Reddy CS. Yadav JS. Synlett 2003, 858

5c Dabkowski W. Tworowska I. Michalski J. Cramer F. Chem. Commun. 1997, 877

5d Prakash GKS. Mathew T. Panja C. Olah GA. J. Org. Chem. 2007, 72: 5847

5e Ryabukhin SV. Plaskon AS. Ostapchuk EN. Volochnyuk DM. Tolmachev AA. Synthesis 2007, 417

5f Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synthesis 2006, 3715

6a Corey EJ. Boaz NW. Tetrahedron Lett. 1985, 26: 6015

6b Bertz SH. Miao G. Rossiter BE. Snyder JP. J. Am. Chem. Soc. 1995, 117: 11023

6c Terang N. Mehta BK. Ila H. Junijappa H. Tetrahedron 1998, 54: 12973

6d Iwai T. Ito T. Mizumo T. Ishino Y. Tetrahedron Lett. 2004, 45: 1083

6e Kobayashi K. Takanohashi A. Hashimoto K. Morikawa O. Konishi H. Tetrahedron 2006, 62: 3158

6f Chen Y.-J. Huang Y.-P. Tetrahedron Lett. 2000, 41: 5233

7a Yamanaka M. Nishida A. Nakagawa M. J. Org. Chem. 2003, 68: 3112

7b Sakai N. Hirasawa M. Hamajima T. Konakahara T. J. Org. Chem. 2003, 68: 483

7c Jiang B. Si YG. Tetrahedron Lett. 2003, 44: 6767

7d Ishino Y. Mihara M. Takeuchi T. Takemoto M. Tetrahedron Lett. 2004, 45: 3503

7e Ryabukhin SV. Plaskon AS. Volochnyuk DM. Tolmachev AA. Synlett 2004, 2287

7f Yoshikawa E. Gevorgyan V. Asao N. Yamamoto Y. J. Am. Chem. Soc. 1997, 119: 6781

8a Bahrami K. Tetrahedron Lett. 2006, 47: 2009

8b Khodaei MM. Bahrami K. Khedri M. Can. J. Chem. 2007, 85: 7

8c Bahrami K. Khodaei MM. Kavianinia I. Synthesis 2007, 547

8d Khodaei MM. Bahrami K. Karimi A. Synthesis 2008, 1682

8e Bahrami K. Khodaei MM. Naali F. J. Org. Chem. 2008, 73: 6835

8f Bahrami K. Khodaei MM. Naali F. Synlett 2009, 569

8g Khodaei MM. Bahrami K. Tirandaz Y. J. Sulfur Chem. 2009, 30: 581

8h Bahrami K. Khodaei MM. Soheilizad M. Synlett 2009, 2773

8i Bahrami K. Khodaei MM. Soheilizad M. J. Org. Chem. 2009, 74: 9287

8j Bahrami K. Khodaei MM. Farrokhi A. Tetrahedron 2009, 65: 7658

8k Bahrami K. Khodaei MM. Tirandaz Y. Synthesis 2009, 369

9 Mohammadpoor-Baltork I. Memarian HR. Bahrami K. Monatsh. Chem. 2004, 135: 411

10 Elson KE. Jenkinsb ID. Loughlin WA. Tetrahedron Lett. 2004, 45: 2491

11 Al-Awadi H. Ibrahim MR. Dib HH. Al-Awadi NA. Ibrahim YA. Tetrahedron 2005, 61: 10507

12 Rahman A.-U. Basha A. Waheed N. Tetrahedron Lett. 1976, 17: 219

13 Gajda T. Zwierzak I. Synthesis 1981, 1005

14 Olah CA. Arvanaghi M. Ohannesian L. Surya PGK. Synthesis 1984, 785

15 Dictionary of Organic Compounds 5th ed., Vol. 1: Buckingham J. Chapman and Hall; London: 1982. p.19

16 Lajis N. Pertanika 1985, 8: 67

17 Masuda R. Hojo M. Ichi T. Sasano S. Kobayashi T. Kuroda C. Tetrahedron Lett. 1991, 32: 1195

18 Ho TL. Synth. Commun. 1979, 9: 37

19 Scheeren JW. Ooms PHJ. Nivard RJF. Synthesis 1973, 149

20a Fieser LF. Fieser M. Reagents for Organic Synthesis Vol. 1: Wiley; New York: 1967. p.333

20b Pedersen BS. Scheibye S. Nilsson NH. Lawesson S.-O. Bull. Soc. Chim. Belg. 1978, 87: 223

20c Pedersen BS. Scheibye S. Clausen K. Lawesson S.-O. Bull. Soc. Chim. Belg. 1978, 87: 293