Octahydro-1H,5H,7H-dipyrrolo[1,2-c:1',2'-f][1,3,6]oxadiazocine-5-thione

A minor byproduct in the reaction of (S)-prolinol with thiophosgene in the presence of triethylamine is identified as a novel tricyclic dipyrrolidino-1,3,6-oxadiazocane-2-thione, the first example of such a ring system, and a representative of the uncommon but useful 1,3,6-oxadiazocanes. A mechanism is proposed for its formation. Publisher PDF