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Synthesis 2010(24): 4282-4286
DOI: 10.1055/s-0030-1258283
DOI: 10.1055/s-0030-1258283
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Trimethylsilyl Chloride Promoted Selective Desulfurization of Thiocarbonyls to Carbonyls with Hydrogen Peroxide
Further Information
Received
23 August 2010
Publication Date:
05 October 2010 (online)
Publication History
Publication Date:
05 October 2010 (online)
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
-
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