SELENOLANES, SELENATRANS AND ESTERS OF SELENIC ACID

Abstract

It is known that selenic acid and selenium dioxide act as oxidizing agents in reactions with α-oxides when heated. The proposed paper presents data on the synthesis of organoselenium compounds based on reactions of α-oxides with selenic acid and its anhydride, where the latter act as selenation agents. It was found that in the presence of catalytic amounts of boron trifluoride esterate in the reactions of oxiranes with acid the oxirane ring opens both according to the rule and against the Krasussky rule with the formation of a mixture of α- and β- isomers of selenic acid esters. In contrast to the acid, the reactions of oxiranes with selendioxide involve the expansion of the oxirane ring to form functionally substituted selenolanes. This paper is followed by the analysis of the literature material on atranes, a unique class of heterocyclic compounds with distinct biologically active properties, and their element derivatives (B, Ge, Si, etc.). For the first time we have synthesized selenatranol, which is not described in the literature. In future it may not only possess bioactive properties in itself, like the majority of organoselenium compounds, but also be a drug precursor. Acetylselenatranol was synthesized by the reaction of selenatranol with acetic anhydride in acid medium. The data of IR, PMR spectra and elemental analysis of the synthesized compounds as well as the data of thermogravimetric (TGA) and differential thermal analysis (DTA) of some of them are given