硫醇氧化成二硫化物的方法

PLEASE SCROLL DOWN FOR ARTICLE This article was downloaded by: CDL Journals Account On: 10 January 2010 Access details: Access Details: subscription number 912375050 Publisher Taylor Fatemeh Derikvand a; Hossein A. Oskooie a; Rahim Hekmat Shoar a; Mahmood Tajbakhsh b a Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran b Department of Chemistry, Mazandaran University, Babolsar, Iran To cite this ArticleTo cite this Article Heravi, Majid M., Derikvand, Fatemeh, Oskooie, Hossein A., Shoar, Rahim Hekmat and Tajbakhsh, Mahmood(2007) Silica-Supported bis (Trimethylsilyl) Chromate: Oxidation of Thiols to Their Corresponding Disulfides, Synthetic Communications, 37: 3, 513 517 To link to this Article: DOI: To link to this Article: DOI: 10.1080/00397910601039267 URL: URL: /10.1080/00397910601039267 Full terms and conditions of use: This article may be used for research, teaching and private study purposes. Any substantial or systematic reproduction, re-distribution, re-selling, loan or sub-licensing, systematic supply or distribution in any form to anyone is expressly forbidden. The publisher does not give any warranty express or implied or make any representation that the contents will be complete or accurate or up to date. The accuracy of any instructions, formulae and drug doses should be independently verified with primary sources. The publisher shall not be liable for any loss, actions, claims, proceedings, demand or costs or damages whatsoever or howsoever caused arising directly or indirectly in connection with or arising out of the use of this material. Silica-Supported bis (Trimethylsilyl) Chromate: Oxidation of Thiols to Their Corresponding Disulfi des Majid M. Heravi, Fatemeh Derikvand, Hossein A. Oskooie, and Rahim Hekmat Shoar Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran Mahmood Tajbakhsh Department of Chemistry, Mazandaran University, Babolsar, Iran Abstract: An effi cient and convenient method for the oxidation of thiols mediated by silica-supported bis (trimethylsilyl) chromate (BTSC) in acetonitrile is reported. Keywords: BTSC, disulfi des, oxidation, solid-supports, thiols Disulfi des are useful reagents in organic synthesis.1,2They are also used in sulphenylation of enolates and other anions,3and they are essential moieties of biologically active compounds for peptide and protein stabili- zation.4 Because disulfi des are relatively more stable to organic reactions such as oxidation, alkylation, and acylation compared to the corresponding free thiols, the thiol group can be protected as a disulfi de. The desired thiol can be generated from the disulfi de either by reduction or by other sulfur sulfur bond cleavage reagents such as CN2, OH2, or hydrazines.5Various reagents for oxidative coupling of thiols to disulfi des are described (e.g., per- manganates,6sodium perborate,7ferric chloride,8sodium chlorite,9 hydrogen peroxide,10halogens,11and others,1217but they encounter the diffi culty of product handling and isolation, Some of these methods Received in the U.K. June 12, 2006 Address correspondence to Majid M. Heravi, Department of Chemistry, School of Sciences, Azzahra University, Vanak, Tehran, Iran. E-mail: mmh1331 Synthetic Communicationsw, 37: 513517, 2007 Copyright # Taylor Nishiyama, Y.; Kambe, N.; Muari, S.; Sonoda, N. Selenium, carbon monoxide and water as a new reduction system: Reductive cleavage of disulfi des and diselenides to thiols and selenols. Tetrahedron Lett. 1987, 28, 3271. 2. Antebi, S.; Alper, H. Cobalt carbonyl catalyzed reactions of disulfi des: Carbonyla- tion to thioesters and desulfurization to sulfi des. Tetrahedron Lett. 1985, 26, 2609. 3. Bioschoff, L.; David, C.; Martin, L.; Meudal, H.; Roques, B.-P.; Fournie- Zaulski, M.-C. 2,4-Dinitrophenyl 4-methoxybenzyl disulfi de: A new effi cient reagent for the electrophilic sulfenylation ofb-amino ester enolates. J. Org. Chem. 1997, 62, 4848. Table 2.Comparison of silica-supported BTSC with some of the other reagents for oxidation of thiophenol and sulfi des EntryReagentTime (min)YieldReferences 1Bu3SnOMe/FeCl31209913 2PCC1149714 3(NH4)S2O8107915 4Caros acid/SiO22709316 5Silica-supported BTSC1598 Oxidation of Thiols515 Downloaded By: CDL Journals Account At: 17:46 10 January 2010 4. Bodansazky, M. Principles of Peptide Synthesis; Springer-Verlag: Berlin, 1984; p. 307. 5. Maiti, S. N.; Spevak, P.; Singh, M. P.; Micetch, R. G. Reductive cleavage of symmetrical disulfi de with hydrazines. Synth. Commun. 198818, 575. 6. 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Bismuth(III) nitrate pentahydrate Bi(NO3)(3).5H2O: An inexpensive and mild reagent for the effi cient and clean oxidation of thiols to disulfi des. Bull. Korean Chem. Soc. 200324, 885. 13. Sato, T.; Otera, J.; Nozaki, H. Activation and synthetic applications of thiostan- naneseffi cient conversion of thiols into disulfi des. Tetrahedron Lett. 199031, 3591. 14. Salehi, P.; Farrokhi, A.; Gholizadeh, M. Oxidative coupling of thiols by pyridi- nium chlorochromate in solution and solvent free conditions. Synth. Commun. 200131, 2777. 15. Varma, R. S.; Meshram, H. M.; Dahiya, R. Solid state oxidation of thiols to disulfi des using ammonium persulfate. Synth. Commun. 200030, 1249. 16. Movassagh, B.; Lakouraj, M. M.; Ghodrati, K. Caros acid supported on silica gel, part 1: Oxidative coupling of thiols to disulfi des. Synth. Commun. 199929, 3597. 17. 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Oxidative deprotection of tetrahydropyranyl ethers to carbonyl compounds with montmorillonite K-10 supported bis(trimethylsilyl) chromate under non-aqueous conditions. J. Chem. Res. 1998, 718. M. M. Heravi et al.516 Downloaded By: CDL Journals Account At: 17:46 10 January 2010 23. Heravi, M. M.; Ajami, D.; Tajbakhsh, M.; Ghassemzadeh, M. Clay-supported bis- (trimethylsilyl)-chromate:An effi cientreagentforoxidativedeoximation. Monatsch. Chem. 2000131, 1109. 24. Heravi, M. M.; Derikvand, F.; Oskooie, H. A.; Hekmatshoar, R. Silica gel supported bis(trimethylsilyl) chromate: Oxidation of 1,4-dihydropyridines to pyridines. Synth. Commun. 200636, 72. 25. Khaleghi, S.; Heravi, M. M.; Drikvand, F. bis(trimethylsilyl) chromate: An effi cient reagent for cleavage of phenylhydrazones. Phosphorus, Sulfur Relat. Elem. 2006181 (1), 227. 26. Heravi, M. M.; Tajbakhsh, M.; Bakooie, H.; Ajami, D. 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