Studies on the unusual stability of cis-2,5-diethoxy-2,5- bis(hydroxymethyl)-1,4-dioxane

Article abstract of DOI:10.1016/S0040-4020(99)00003-4

Almost equal amounts of the trans and cis isomers of 2,5-diethoxy-2,5- bis(hydroxymethyl)-1,4-dioxane (2trans and 2cis) are obtained by treating dihydroxyacetone with acidic ethanol. To explain the formation of an unusually large quantity of 2cis, conformation analyses and equilibration experiments were performed for the related compounds. The results indicate that the stability of 2cis derives not from the hydroxymethyl groups but from the unusually stable twist-boat conformation. The factors stabilizing the twist-boat conformation in 2cis were discussed.