Conformational Analysis of Trimethylene Sulfites. The Importance of Vicinal Unshared Electron Pairs

Abstract

Dipole moments are reported for trimethylene sulfite and 11 alkyl derivatives in a variety of solvents (C6H12, CCl4, C6H6, dioxan). The variation of dipole moment with solvent for one of the 5-t-butyltrimethylene sulfite isomers is confirmed, but this behavior is not shown by the other compounds. This latter fact is used to rule out rapid chair–chair interconversion for these compounds. Recent ultrasonic absorption experiments are reinterpreted in the context of vicinal electron pair interactions and their effect on conformational analysis of sulfites and similar six-membered compounds. The result is a general scheme which is consistent with available information and which we believe is preferable to analysis of these compounds by analogy with cyclohexane.