Efficient Synthesis of Functionalized Unsymmetrical Dialkyl Trisulfanes

Slawomir Lach; Dariusz Witt

doi:10.1055/s-0033-1338966

Synlett, Inhaltsverzeichnis

Synlett 2013; 24(15): 1927-1930
DOI: 10.1055/s-0033-1338966

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Efficient Synthesis of Functionalized Unsymmetrical Dialkyl Trisulfanes

Slawomir Lach

Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland Fax: +48(58)3472694 eMail: dwitt@chem.pg.gda.pl

,

Dariusz Witt*

Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-233 Gdansk, Poland Fax: +48(58)3472694 eMail: dwitt@chem.pg.gda.pl

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Abstract

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Abstract

We have developed a convenient method for the synthesis of functionalized unsymmetrical dialkyl trisulfanes under mild conditions in very good yields. The designed method is based on the reaction of (5,5-dimethyl-2-thioxo-1,3,2-dioxaphosphorinan-2-yl)-disulfanyl derivatives with alkyl disulfanyl anions generated in situ from S-acetyl disulfanyl derivatives and sodium methoxide. The developed method allows for the preparation of unsymmetrical trisulfanes bearing additional hydroxyl, carboxyl, or amino functionalities on both sides of the trisulfane functionality.

Key words

unsymmetrical trisulfanes - thiols - hydrodisulfanes - S-acetyl alkyldisulfanes - phosphorodithioic acid

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Referenzen

References
1 Ford PW, Narbut MR, Davidson BS. J. Org. Chem. 1994; 59: 5955
2 Nicolaou KC, Dai WM. Angew. Chem., Int. Ed. Engl. 1991; 30: 1387
3 Steudel R. Chem. Rev. 2002; 102: 3905

4a Chen C.-C, Ho C.-T. J. Agric. Food Chem. 1986; 34: 830
4b Chen C.-C, Chen S.-D, Chen J.-J, Wu C.-M. J. Agric. Food Chem. 1984; 32: 999

5 Rajanikanth B, Ravindranath B, Shankaranarayana ML. Phytochemistry 1984; 23: 899
6 Näf R, Velluz A. Flavour Fragr. J. 1996; 11: 295
7 Block E. Angew. Chem., Int. Ed. Engl. 1992; 31: 1135
8 Lawson LD, Wang Z.-Y, Hughes BG. Planta Med. 1991; 57: 363
9 Moore RE. Chem. Commun. 1971; 1168
10 Fletcher JC, Robson A. Biochem. J. 1963; 87: 553
11 Jespersen AM, Christensen T, Klausen NK, Nielsen PF, Sorensen HH. Eur. J. Biochem. 1994; 219: 365
12 Andersson C, Edlund PO, Gellerfors P, Hansson Y, Holmberg E, Hult C, Johansson S, Kordel J, Lundin R, Mended-Hartvig I, Noren B, Wehler T, Widmalm G, Ohman J. Int. J. Pept. Protein Res. 1996; 47: 311
13 Canova-Davis E, Baldonado IP, Chloupek RC, Ling VT, Gehant R, Olson K, Gillece-Castro BL. Anal. Chem. 1996; 68: 4044
14 Lee MD, Dunne TS, Chang CC, Ellestad GA, Siegel MM, Morton GO, McGahren WJ, Borders DB. J. Am. Chem. Soc. 1987; 109: 3464
15 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
16 Golik J, Dubay G, Groenewold G, Kwaguchi H, Konishi M, Krishnan B, Okhuma H, Saito K, Doyle TW. J. Am. Chem. Soc. 1987; 109: 3462
17 Kumar RA, Ikemoto N, Patel DJ. J. Mol. Biol. 1997; 265: 173

18a Zysman-Colman E, Harpp DN. J. Org. Chem. 2003; 68: 2487
18b Clayton JO, Etzler DH. J. Chem. Soc. 1974; 69: 974

19 Fuson RC, Price CC, Burness DM, Foster RE, Hatchard WR, Lipscomb RD. J. Org. Chem. 1946; 11: 487
20 Sato R, Saito S, Chiba H, Goto T, Saito M. Chem. Lett. 1986; 349
21 Schimmelschmidt K, Hoffmann H, Mundlos E. Chem. Ber. 1963; 96: 38
22 Buckman JD, Field L. J. Org. Chem. 1967; 32: 2
23 Mott AW, Barany G. Synthesis 1984; 657
24 Hayashi S, Furukawa M, Yamamoto J, Hamamura K. Chem. Pharm. Bull. 1967; 15: 1310
25 Capozzi G, Capperucci A, Degl’Innocenti A, Del Duce R, Menichetti S. Tetrahedron Lett. 1989; 30: 2991

26a Arisawa M, Tanaka K, Yamaguchi M. Tetrahedron Lett. 2005; 46: 4797
26b Hou Y, Abu-Yousef IA, Doung Y, Harpp DN. Tetrahedron Lett. 2001; 42: 8607

27 Harpp DN, Granata A. Tetrahedron Lett. 1976; 3001
28 Wu Z, Back TG, Ahmad R, Yamdagni R, Amstrong DA. J. Phys. Chem. 1982; 86: 4417
29 An H, Zhu J, Wang X, Xu X. Bioorg. Med. Chem. Lett. 2006; 16: 4826
30 Nakabayashi T, Tsurugi J. J. Org. Chem. 1961; 26: 2482
31 Böhme H, Van Ham G. Justus Liebigs Ann. Chem. 1958; 617: 62
32 Abu-Yousef IA, Rys AZ, Harpp DN. J. Sulfur Chem. 2006; 27: 15
33 Harpp DN, Derbesy G. Tetrahedron Lett. 1994; 35: 5381
34 Kresze G, Patzscheke J. Chem. Ber. 1960; 93: 380
35 Antoniow S, Witt D. Synthesis 2007; 363
36 Kowalczyk J, Barski P, Witt D, Grzybowski BA. Langmuir 2007; 23: 2318
37 Szymelfejnik M, Demkowicz S, Rachon J, Witt D. Synthesis 2007; 3528
38 Demkowicz S, Rachon J, Witt D. Synthesis 2008; 2033
39 Okragla E, Demkowicz S, Rachon J, Witt D. Synthesis 2009; 1720
40 Kertmen A, Lach S, Rachon J, Witt D. Synthesis 2009; 1459
41 Lach S, Sliwka-Kaszynska M, Witt D. Synlett 2010; 2857

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