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 2009(9): 1459-1462
DOI: 10.1055/s-0028-1088161
DOI: 10.1055/s-0028-1088161
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New York
Novel and Efficient Methods for the Synthesis of Symmetrical Trisulfides
Weitere Informationen
Received
5 November 2008
Publikationsdatum:
25. März 2009 (online)
Publikationsverlauf
Publikationsdatum:
25. März 2009 (online)
![](https://www.thieme-connect.de/media/synthesis/200909/lookinside/thumbnails/10.1055-s-0028-1088161-1.jpg)
Abstract
We have developed convenient methods for the synthesis of symmetrical trisulfides under mild conditions in very good yields. The described methods are based on the straightforward preparation of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorin-2-yl)disulfanyl derivatives from readily available 5,5-dimethyl-2-sulfanyl-2-thioxo-1,3,2-dioxaphosphorinane or bis(5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl) disulfide. The symmetrical trisulfides can be obtained from aliphatic and aromatic thiols and also l-cysteine derivatives.
Key words
symmetrical trisulfides - thiols - sulfenyl bromides - l-cysteine
-
1a
Higuchi O.Tateshita K.Nishimura H. J. Agric. Food Chem. 2003, 51: 7208 -
1b
Schregen L.Diriack P.Van Wassehove F.Schamp N. J. Agric. Food Chem. 1976, 24: 336 - 2
Nicolaou KC.Hummel CW.Nakada M.Shibayama K.Pitsinos EN.Saimoto H.Mizuno Y.Baldenius K.-U.Smith AL. J. Am. Chem. Soc. 1993, 115: 7625 - 3
Kumar RA.Ikemoto N.Patel DJ. J. Mol. Biol. 1997, 265: 173 - 4
Schöberl A.Wagner A. In Houben-Weyl 4th ed., Vol. 9:Müller E. Georg Thieme Verlag; Stuttgart: 1955. p.87-90 -
5a
Zysman-Colman E.Harpp DN. J. Org. Chem. 2003, 68: 2487 -
5b
Clayton JO.Etzler DH. J. Am. Chem. Soc. 1947, 69: 974 - 6
Fuson RC.Price ChC.Burness DM.Foster RE.Hatchard WR.Lipscomb RD. J. Org. Chem. 1946, 11: 487 - 7
Sato R.Saito S.Chiba H.Goto T.Saito M. Chem. Lett. 1986, 349 - 8
Schimmelschmidt K.Hoffmann H.Mundlos E. Chem. Ber. 1963, 96: 38 - 9
Buckman JD.Field L. J. Org. Chem. 1967, 32: 2 - 10
Mott AW.Barany G. Synthesis 1984, 657 - 11
Hayashi S.Furukawa M.Yamamoto J.Hamamura K. Chem. Pharm. Bull. 1967, 15: 1310 - 12
Capozzi G.Capperucci A.Degl’Innocenti A.Del Duce R.Menichetti S. Tetrahedron Lett. 1989, 30: 2991 -
13a
Arisawa M.Tanaka K.Yamaguchi M. Tetrahedron Lett. 2005, 46: 4797 -
13b
Hou Y.Abu-Yousef IA.Doung Y.Harpp DN. Tetrahedron Lett. 2001, 42: 8607 - 14
Harpp DN.Granata A. Tetrahedron Lett. 1976, 17: 3001 - 15
Wu Z.Back TG.Ahmad R.Yamdagni R.Amstrong DA. J. Phys. Chem. 1982, 86: 4417 - 16
An H.Zhu J.Wang X.Xu X. Bioorg. Med. Chem. Lett. 2006, 16: 4826 - 17
Nakabayashi T.Tsurugi J. J. Org. Chem. 1961, 26: 2482 - 18
Böhme H.Van Ham G. Justus Liebigs Ann. Chem. 1958, 617: 62 - 19
Harpp DN.Derbesy G. Tetrahedron Lett. 1994, 35: 5381 - 20
Kresze G.Patzscheke J. Chem. Ber. 1960, 93: 380 - 21
Antoniow S.Witt D. Synthesis 2007, 363 - 22
Kowalczyk J.Barski P.Witt D.Grzybowski BA. Langmuir 2007, 23: 2318 - 23
Szymelfejnik M.Demkowicz S.Rachon J.Witt D. Synthesis 2007, 3528 - 24
Demkowicz S.Rachon J.Witt D. Synthesis 2008, 2033 - 25
Pappo D.Kashman Y. Org. Lett. 2006, 8: 1177 - 26
Edmundson RS. Tetrahedron 1965, 21: 2379 - 27
Carmona E.Contreras L.Sanches LJ.Gutierrez-Puebla E.Monge A. J. Chem. Soc., Dalton Trans. 1989, 2003 - 28
Kohama Y.Iida K.Semba T.Mimura T.Inada A. Chem. Pharm. Bull. 1992, 40: 2210