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EN
The reactions of aryl isoselenocyanates 1 with 3-chloropropan-1-ol (8) in the presence of sodium hydride in dichloromethane at room temperature gave 1,3-oxaselenan-2-imines 10 in fair yield. A reaction mechanism via nucleophilic attack of the alcoholate at the isoselenocyanate 1, followed by an 6-exo-tet cyclization, is most likely.
EN
The reactions of cyclic selenenamides: benzisoselenazol-3(2H)-ones and 1,3,2-benzodiselenazoles 3 with living cell nucleophiles such as water and thiols were investigated. Both of them caused Se–N bond cleavage. The thiolysis of 1 led to selenosulphides 6, 9 or to products of their disproportionation the equimolar mixtures of diselenides 7 and disulphides 8. The hydrolysis of 1 and 3 as well as thiolysis of 3 resulted in formation of corresponding diaryl diselenides 7 or 10.
EN
The reactions of two o-substituted bromoselenobenzenes: 2-(bromoseleno)benzene sulfonyl chloride and 1,2-di(bromoseleno)benzene with bisnucleophiles having amino, thiol and active methylene group have been studied. In most cases five membered rings, containing selenium as well as nitrogen and sulfur atoms, such as 1,3,2-benzothiaselenazole, 1,2,3-dithiaselenazole, benzo-1,3(2H)-thiaselenole, 1,3,2-benzodiselenazole and benzo-1,3(2H)-diselenole, were formed. The elaborated procedures have synthetic value.
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