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Organoselenium Chemistry. Synthesis of Selenetan-3-ol, 1-Bromo-3-selenocyanatopropan-2-ol and 2-Benzylseleno-Substituted Fumaric and Succinic Acids

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Arnold, AP and Canty, AJ (1983) Organoselenium Chemistry. Synthesis of Selenetan-3-ol, 1-Bromo-3-selenocyanatopropan-2-ol and 2-Benzylseleno-Substituted Fumaric and Succinic Acids. Australian Journal of Chemistry, 36 (5). pp. 815-823. ISSN 0004-9425

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Abstract

Approaches to the synthesis of diselenols have led to isolation of several new organoselenium compounds. Removal of mercury, as HgS, from [1,3-diselenylpropan-2-olato(2-)-Se,Se' ]mercury(II) results in decomposition of the organoselenium fragment to selenetan-3-ol. 1,3-Dibromopropan-2-0l reacts with KSeCN to form 1-bromo-3-selenocyanatopropan-2-0l; the selenoethers 2-(benzyl- se1eno)fumaric acid [(Z)-PhCH2SeC(C02H)=CHC02H] and 2-(benzylse1eno)succinic acid [PhCH2SeCH(C02H)CH2C02H] are formed by base-catalysed reaction of phenylmethaneselenol with acetylenedicarboxylic acid and maleic acid, respectively. The conformations adopted by PhCH2XCH(C02H)CH2C02H (X = S, Se) in acetone have been determined by 1H n.m.r. spectroscopy.

Item Type: Article
Journal or Publication Title: Australian Journal of Chemistry
Page Range: pp. 815-823
ISSN: 0004-9425
Identification Number - DOI: 10.1071/CH9830815
Date Deposited: 31 Jan 2008 22:09
Last Modified: 18 Nov 2014 03:27
URI: http://eprints.utas.edu.au/id/eprint/2927
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