1,8-Dioxa-4,11-dithiacyclotetradecane-2,9-dione

The title compound, C10H16O4S2, was formed in a reaction of allyl alcohol a nd thioglycolic acid followed by acid-catalyzed esterification of the resul ting hydroxy acid. The compound forms triclinic crystals and there is an in version center in the middle of the molecule The structure was determined t o be a 14-membered dilide which in the solid state assumes a centrosymmetri c conformation where the S-C-C-O-C-C-C-S chain is roughly gauche-gauche-ant i-anti-gauche-anti-gauche. Molecular-mechanics calculations showed that the X-ray conformation is 10 kJ above the global minimum.