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Synthesis 2011(2): 277-280
DOI: 10.1055/s-0030-1258331
DOI: 10.1055/s-0030-1258331
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Silver Nitrate Catalyzed Oxidation of Sulfides
Further Information
Received
8 October 2010
Publication Date:
15 November 2010 (online)
Publication History
Publication Date:
15 November 2010 (online)
Abstract
A variety of sulfides were converted into the corresponding sulfoxide derivatives with 70% tert-butyl hydroperoxide in water as the oxidant in the presence of catalytic quantity of silver nitrate. The method described has a wide range of application, does not involve cumbersome workup, exhibits chemoselectivity, and proceeds under mild reaction conditions, and the resulting products are obtained in good yields within a reasonable time.
Key words
oxidation - sulfide - sulfoxide - silver nitrate - tert-butyl hydroperoxide
- Supporting Information for this article is available online:
- Supporting Information
- 1
Sheldon RA.Kochi JK. Metal-Catalyzed Oxidation of Organic Compounds Academic Press; New York: 1981. -
2a
Cremlyn RJ. An Introduction to Organosulfur Chemistry John Wiley and Sons; Chichester: 1996. -
2b
Drabowski J.Kielbasinski P.Mikolajczyk M. Synthesis of Sulfoxides John Wiley and Sons; New York: 1994. -
2c
The
Synthesis of Sulphones, Sulphoxides, and Cyclic Sulphides
Capozzi G.Patai S.Rappoport Z. John Wiley and Sons; New York: 1994. -
3a
Legros J.Dehli J.Bolm C. Adv. Synth. Catal. 2005, 347: 19 -
3b
Carreno MC. Chem. Rev. 1995, 95: 1717 -
3c
Fernández N.Khiar I. Chem. Rev. 2003, 103: 3651 -
4a
Khan MH.Hussany SM.Khan MA.Ali A. Radiochim. Acta 1994, 65: 239 -
4b
Shukla JP.Singh RK.Sawant SR.Varadarajan N. Anal. Chim. Acta 1993, 276: 181 -
5a
Salas M.Ward A.Caro J. BMC Gastroenterol. 2002, 2: 17 ; http://www.biomedcentral.com/bmcgastroenterol/ -
5b
Spencer CM.Faulds D. Drugs 2000, 60: 321 - 6
Perez-Giraldo C.Cruz-Villalon G.Sanchez-Silos R.Martinez-Rubio R.Blanco MT.Gomez-Garcia AC.
J. Appl. Microbiol. 2003, 95: 709 - 7
Merino G.Molina AJ.Garcia JL.Pulido MM.Prieto JG.Alverez AI. J. Pharm. Pharmacol. 2003, 55: 757 - 8
Kotelanski B.Grozmann RJ.Cohn JN. Clin. Pharmacol. Ther. 1973, 14: 427 - 9
Scimied R.Wang GX.Korth M. Circ. Res. 1991, 68: 597 - 10
Lechin F.Van der Dijis B.Pardey-Maldonado B.John E.Jimenez V.Orozco B.Baez S.Lechin ME. J. Med. 2000, 31: 333 - 11
Padmanabhan S.Lavin RC.Durant GJ. Tetrahedron: Asymmetry 2000, 11: 3455 -
12a
Bagherzadeh M.Latifi R.Tahsini L.Amini M. Catal. Commun. 2008, 10: 196 -
12b
Karimi B.Nezhad MG.Clark JH. Org. Lett. 2005, 7: 625 -
12c
Hajipour AR.Ruoho AE. Sulfur Lett. 2003, 26: 83 -
12d
Bravo A.Dordi B.Fontana F.Minisci F. J. Org. Chem. 2001, 66: 3232 - 13
Venier CG.Squires TG.Chen YY.Hussmann GP.Shei JC.Smith BF. J. Org. Chem. 1982, 47: 3773 - 14
Gasparrini F.Giovannoli M.Maresca L.Natile G.Palmieri G. Synth. Commun. 1984, 14: 1111 - 15
Lakouraj MM.Tajbakhsh M.Shirini F.Asady Tamani MV. Synth. Commun. 2005, 35: 775 -
16a
Shukla VG.Salgaonkar PD.Akamanchi KG.
J. Org. Chem. 2003, 68: 5422 -
16b
Tohama H.Takizawa S.Watanabe H.Kita Y. Tetrahedron Lett. 1998, 39: 4547 -
16c
Xia M.Chen ZC. Synth. Commun. 1997, 27: 1315 -
17a
Romanelli GP.Bennardi DO.Palermo V.Vázquez PG.Tundo P. Lett. Org. Chem. 2007, 4: 544 -
17b
Trivedi R.Lalitha P. Synth. Commun. 2006, 36: 3777 -
17c
Di Furia F.Modena G.Curci R. Tetrahedron Lett. 1976, 17: 4637 - 18
Stanger KJ.Wiench JW.Pruski M.Espenson JH.Kraus GA.Angelici RJ. J. Mol. Catal. A: Chem. 2006, 243: 158 -
19a
Egami H.Katsuk T. J. Am. Chem. Soc. 2007, 129: 8940 -
19b
Baciocchi E.Gerini MF.Lapi A. J. Org. Chem. 2004, 69: 3586 -
19c
Legros J.Bolm C. Angew. Chem. Int. Ed. 2003, 42: 5487 -
19d
Marques A.Marin M.Ruasse MF. J. Org. Chem. 2001, 66: 7588 -
20a
Barker JE.Ren T. Tetrahedron Lett. 2005, 46: 6805 -
20b
Xie F.Fu ZH.Zhong S.Ye ZP.Zhou XP.Liu FL.Rong CY.Mao LQ.Yin DL. J. Mol. Catal. A: Chem. 2009, 307: 93 - 21
Iwamoto M.Tanaka Y.Hirosumi J.Kita N.Triwahyono S. Microporous Mesoporous Mater. 2001, 48: 271 - 22
Conte V.Fabbianesi F.Floris B.Galloni P.Sordi D.Arends ICWE.Bonchio M.Rehder D.Bogdal D. Pure Appl. Chem. 2009, 81: 1265 - 23
Shi F.Tse MK.Kaiser HM.Beller M. Adv. Synth. Catal. 2007, 349: 2425 - 24
Pearl IA. Org. Synth. 1963, 4: 972 - 25
Campaigne E.LeSuer WM. Org. Synth. 1963, 4: 919 - 26
Chakraborty D.Gowda RR.Malik P. Tetrahedron Lett. 2009, 50: 6553