Abstract
Abstract Conformational analysis of 1,3,5-trithiane derivatives with sulfur-substituents was carried out with the aid of PMR spectra at various temperatures. 2-Phenylthio-1,3,5-trithiane exhibited the strong anomeric effect whereas 2-phenylthiothiane the moderate. This enhanced anomeric effect in trithiane derivatives was attributed to both the stabilization of the axial form and the destabilization of the equatorial form. cis-2,4-Bis(phenylthio)-1,3,5-trithiane was found to possess a diaxial conformation to a fair extent in support of the presence of the strong anomeric effect. Equilibration between cis and trans forms of 2,4-bis(phenylthio)-1,3,5-trithiane was carried out to show that the trans form was more stable than the cis. The barrier to inversion of trans-2,4-bis(phenylthio)-1,3,5-trithiane was obtained as ca. 11 kcal/mol.
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