ACID-BASE REACTIONS OF 1,3,4-THIADIAZOLINES AND THIOCARBONYL YLIDES; 1,3,4-THIADIAZOLINE-2-SPIRO-2'-ADAMANTANE

Article abstract of DOI:10.1016/S0040-4039(00)98510-1

The surprising formation of C₂₂H₃₂N₂S₂ from the title compound 1 at 45 ^oC involves the interaction of the basic adamantanethione S-methylide (2) with its acidic precursor 1, in the course of which the anion 6 undergoes electrocyclic ring opening; the acid and base functions offer the clue to a prolific chemistry of the thiadiazoline 1 and the thiocarbonyl ylide 2.