ORGANOSELENIUM CHEMISTRY - SYNTHESIS OF SELENETAN-3-OL, 1-BROMO-3-SELENOCYANATOPROPAN-2-OL AND 2-BENZYLSELENO-SUBSTITUTED FUMARIC AND SUCCINIC ACIDS

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-ol reacts with KSeCN to form 1-bromo-3-selenocyanatopropan-2-ol; the selenoethers 2-(benzyl-seleno)fumaric acid [(Z)-PhCH2SeC(C02H)=CHCO2H] and 2-(benzylse1eno)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. © 1983 ASEG.