REACTIONS OF STEREOISOMERIC 3,4-EPOXYCARANES WITH THIOUREA

Research in the field of organic sulfur compounds has not lost its relevance in recent decades due to interesting features of the reactions, the prospect of wide application of organosulfur compounds in various spheres of human activity and the significant role of this biogenic element in the life of humans and other living organisms. The aim of this study is to investigate the behavior of stereoisomeric 3,4-epoxycaranes with thiourea in basic, neutral and acidic media. When studying the reactions of α- and β-3,4-epoxycaranes with thiourea in sodium ethylate, it was found that in each case the reaction leads to the formation of a single product: at room temperature, crystalline di(caraniol) sulfides are formed in small quantities, and upon heating the reactions are completed. In reactions with thiourea in the absence of a base, both isomers form two products in a ratio of ~ 3:1. Comparison of the spectral characteristics of the dominant (less polar) products showed that they are the same substance, di(10-carene-3-yl) disulfide; for the minor products, structures of 4(10-carene-3-yl)dithiocarane-3-ols were proposed. The study of the behavior of stereoisomeric epoxycaranes with thiourea was continued by carrying out thiylation reactions in the presence of sulfuric acid. We found that these reactions are a convenient way to obtain stereoisomeric thiiranes of the carane series. Attempts to obtain 3,4-epithiocaranes in neutral or basic media did not yield the target products.In order to expand the arsenal of new sulfur-containing compounds of the terpene series, we studied the synthetic capabilities of 3,4-epithiocaranes in nucleophilic addition reactions of sulfur-containing reagents.