RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2002(17): 2513-2516
DOI: 10.1055/s-2002-35634
DOI: 10.1055/s-2002-35634
PAPER
© Georg Thieme Verlag Stuttgart · New York
Trimethylchlorosilane (TMSCl) and Cyanuric Chloride (CC) Catalyzed Efficient Oxidative Coupling of Thiols with Dimethylsulfoxide
Weitere Informationen
Received
26 June 2002
Publikationsdatum:
20. November 2002 (online)
Publikationsverlauf
Publikationsdatum:
20. November 2002 (online)
![](https://www.thieme-connect.de/media/synthesis/200217/lookinside/thumbnails/10.1055-s-2002-35634-1.jpg)
Abstract
Different types of thiols were rapidly and efficiently converted to disulfides using DMSO in the presence of catalytic amounts of either trimethylchlorosilane (TMSCl) or cyanuric chloride (CC).
Key words
thiols - disulfides - oxidative coupling
- 1
Jocelyn DC. In Biochemistry of the Thiol Groups Academic Press; New York: 1992. - 2
Capozzi G.Modena G. In The Chemistry of the Thiol GroupPatai S. Wiley; New York: 1974. Part 2. p.785 -
3a
Noureldin MC.Hendry J.Lee DG. Synthesis 1998, 1587 -
3b
Firouzabadi H.Abbassi M.Karimi B. Synth. Commun. 1999, 29: 2527 -
3c
Kesavan V.Bonnet-Delpon D.Begue JP. Synthesis 2000, 223 -
3d
Fujihara H.Akashi R.Furukawa N. Bull. Chem. Soc. Jpn. 1989, 62: 616 -
3e
Meshram HM.Kache R. Synth. Commun. 1997, 27: 2403 -
3f
Lu G.Zhang Y. Synth. Commun. 1998, 28: 4479 -
3g
McKillop A.Koyuneu D. Tetrahedron Lett. 1990, 31: 5007 -
3h
Karimi B.Zareyee D. Synlett 2002, 346 -
4a
Iranpoor N.Salehi P.Shiriny F. Org. Prep. Proced. Int. 1995, 27: 216 -
4b
Scrivens G.Gilbert BC.Lee CPT. J. Chem. Soc., Perkin Trans 2 1995, 995 -
4c
Iranpoor N.Zeynizadeh B. Synthesis 1999, 49 -
4d
Iranpoor N.Firouzabadi H.Zolfigol MA. Synth. Commun. 1998, 28: 367 -
4e
Raghavan S.Rajender A.Joseph SC.Rasheed MA. Synth. Commun. 2001, 31: 1477 -
4f
Choi J.Yoon NM. J. Org. Chem. 1995, 60: 3266 -
4g
Arterburn JB.Perry MC.Nelson SL.Dible BR.Holguin MS. J. Am. Chem. Soc. 1997, 119: 9309 -
5a
Yiannios CN.Karabinos JV. J. Org. Chem. 1963, 28: 3246 -
5b
Wallace TJ. Chem. Ind (London) 1964, 501 -
5c
Wallace TJ. J. Am. Chem. Soc. 1964, 86: 2018 -
5d
Wallace TJ.Mahon JJ. J. Am. Chem. Soc. 1964, 86: 4099 -
5e
Wallace TJ.Mahon JJ. J. Org. Chem. 1965, 30: 1502 -
5f
Wallace TJ.Weiss HA. Chem. Ind. (London) 1966, 1558 - 6
Mancuso AJ.Swern D. Synthesis 1981, 165 - 7
Senier A. Ber. 1886, 19: 311 - 8
Venkataraman K.Wagle DR. Tetrahedron Lett. 1979, 3037 - 9
Venkataraman K.Wagle DR. Tetrahedron Lett. 1980, 21: 1893 - 10
Falorni M.Porcheddu A.Taddei M. Tetrahedron Lett. 1999, 40: 4395 - 11
Forbes DC.Barrett EJ.Lewis DL.Smith MC. Tetrahedron Lett. 2000, 41: 9943 - 12
Manhas MS.Bose AK.Kajavi MS. Synthesis 1981, 209 - 13
Olah GA.Fung AP.Gupta BGB.Narang SC. Synthesis 1980, 221 - 14
De Luca L.Giacomelli G.Porcheddu A. Org. Lett. 2002, 4: 553 ; and references cited therein - 15
De Luca L.Giacomelli G.Porcheddu A. J. Org. Chem. 2001, 66: 7907 - 16
Groebel W. Chem. Ber. 1960, 93: 284 - 17
Cohen VI. Helv. Chim. Acta 1976, 59: 840 - 18
Liu KT.Tong YC. Synthesis 1978, 669 - 19
Ramadas K.Srinivasan N. Synth. Commun. 1995, 25: 227