The products of the addition of nucleophiles (alcohols, amines) to the cyano group of 5‐(cyanoimino)thiadiazolines 1 undergo a Boulton‐Katritzky rearrangement. The thiadiazoles 4 are formed by subsequent nitrile elimination. In the case of bicyclic thiadiazoloazepine 5 an equilibrium mixture of unrearranged iminothiadiazoline 6 and rearranged thiadiazole 7 is obtained as an intermediate.
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Sonnenschein et al. (1994) studied this question.
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