<i>Se</i>-Aryl Alkane- or Arenecarboselenothioates: Synthesis and Some Reactions

Abstract

Abstract A series of Se-aryl carboselenothioates 3 (RCSSeAr, R=alkyl, aryl) were synthesized and characterized from the reaction of bis(thioacyl) sulfides 1 with sodium areneselenolates. The thionselenolesters 3 are stable (liquid or crystals) both thermally and to moisture. Reactions of 3 with aliphatic primary and secondary amines gave the corresponding ammonium carbodithioates 8 together with diphenyl diselenide 7. In contrast, treatment with aromatic amines or sodium alcoholates afforded the corresponding thioamides or O-alkyl or O-aryl thionesters in good yields. The oxidation of 3 with m-chloroperbenzoic acid gave the corresponding sulfides 12 [RCS(O)SeAr] and acyl arylseleno sulfides 13 [RCOSSeAr] which are formed by a rearrangement of the ArSe group to the thiocarbonyl sulfur atom.