Conformational behaviour of trans-2,3-bis(R-thio)-1,4-dioxanes

Article abstract of DOI:10.1016/S0040-4039(00)94691-4

The conformation of eight trans-2,3-bis(R-thio)-1,4-dioxanes has been studied in chloroform solution using ¹H NMR techniques. Among the alkylthio substituted compounds, the population of diaxial conformer increases from methylthio (71%) to tert-butylthio (85%). The arylthio substituted compounds exist largely as diaxial conformers (ca 90%). The alleviation of anomeric effects in trans-2,3-bis(R-oxy)-1,4-dioxanes bearing bulky alkoxy groups is discussed at the light of these results.