Solid-state rearrangement of some 1,3,2,4-dithiadiazoles to their 1,2,3,5 analogues

Abstract

A variety of 1,3,2,4-dithiadiazoles [m- and p-C₆H₄([graphic omitted])₂ and 1,3,5-C₆H₃([graphic omitted])₃] undergo solid-state rearrangement to their 1,2,3,5-dithiadiazole analogues. This isomerisation process has been examined using differential scanning calorimetry, X-ray powder diffraction techniques and both infrared and electron-spin resonance spectroscopy. A common mechanism is proposed for the rearrangement, involving head-to-tail S ⋯ N and S ⋯ S interactions between dithiadiazole rings.