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Synthesis 2005(3): 447-457  
DOI: 10.1055/s-2004-837289
PAPER
© Georg Thieme Verlag Stuttgart · New York

Odorless Diphenyl Diselenide and Disulfide: Syntheses and Applications

Pranab K. Patra, Kandasamy Shanmugasundaram, Manabu Matoba, Kiyoharu Nishide, Tetsuya Kajimoto, Manabu Node*
Department of Pharmaceutical Manufacturing Chemistry, Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414, Japan
Fax: +81(75)5954775; e-Mail: node@mb.kyoto-phu.ac.jp;
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Publication History

Received 8 September 2004
Publication Date:
16 December 2004 (online)

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Abstract

Bis[4-(trimethylsilyl)phenyl]diselenide (3) and bis[4-(trimethylsilyl)phenyl]disulfide (31) are found to be odorless equivalents of the commonly used diphenyl diselenide and diphenyl di­sulfide, respectively. The diselenide 3 is shown to be useful in the preparation of odorless selenium(II) chloride 26 and selenium(IV) trichloride 28 that follow similar reactivity patterns to their phenyl derivatives and can be stored refrigerated under dry conditions. The corresponding selenium(II) bromide had to be prepared fresh from 3 before use. It is also shown that the trimethylsilyl group in the sulfide products can be protodesilylated quantitatively using TFA.

Key words

odorless - diselenide - disulfide - elimination

19

4-Trimethylsilylphenyl selenium chloride(26) was obtained as dark red colored liquid, however in the presence of moist air, it rapidly decomposes to insoluble yellow solid (mp 235-240 °C), presumably the corresponding seleninic acid.