Abstract
The reaction of adamantanethione (1) and an organic azide at 80°C ("two-component reaction") yields the symmetrical 1,2,4-trithiolane 9 and the corresponding adamantylidene imine 10 in nearly equal amounts. Under the same conditions, the "three-component reaction" with 1, phenyl azide and an aromatic thioketone gives the unsymmetrical 1,2,4-trithiolane 12 as the major product, and 9 and imine 13 as by-products. A 1,3-dipolar cycloaddition of an intermediate thiocarbonyl-S-sulfide and a thioketone is proposed as the mechanism for the formation of the trithiolanes. The structure of trithiolane 12a has been established by X-ray crystallography.
Mloston, Grzegorz