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Synthesis 2009(9): 1459-1462  
DOI: 10.1055/s-0028-1088161
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Novel and Efficient Methods for the Synthesis of Symmetrical Trisulfides

Ahmet Kertmenb, Slawomir Lacha, Janusz Rachona, Dariusz Witt*a
a Department of Organic Chemistry, Chemical Faculty, Gdansk University of Technology, Narutowicza 11/12, 80-952 Gdansk, Poland
Fax: +48(58)3472694; e-Mail: dwitt@chem.pg.gda.pl;
b Chemistry Department, Faculty of Arts and Sciences, Osmangazi University, 26040 Eskisehir, Turkey
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Publication History

Received 5 November 2008
Publication Date:
25 March 2009 (online)

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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