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Article << Previous     |     Next >>   Contents Vol 36(4)

Organoselenium chemistry. Synthesis of selenetan-3-ol, 1-bromo-3-selenocyanatopropan-2-ol and 2-benzylseleno-substituted fumaricand succinic acids

AP Arnold and AJ Canty

Australian Journal of Chemistry 36(4) 815 - 823
Published: 1983


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,Sel]-mercury(II) results in decomposition of the organoselenium fragment to selenetan-3-ol, 1,3-Dibromopropan-2-ol reacts with KSeCN to form 1-bromo-3-selenocyanatopropan-2-ol; the selenoethers 2-(benzyl- se1eno)fumaric acid [(Z)-PhCH2SeC(CO2H)=CHCO2H] and 2-(benzylseleno)succinic acid [PhCH2SeCH(CO2H)CH2CO2H] are formed by base-catalysed reaction of phenylmethaneselenol with acetylenedicarboxylic acid and maleic acid, respectively. The conformations adopted by PhCH2XCH(CO2H)CH2CO2H (X = S, Se) in acetone have been determined by 1H n.m.r. spectroscopy.

Full text doi:10.1071/CH9830815

© CSIRO 1983

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