V. Waagen et al., DIHYDROXYACETONE DIMERS - SOLUTION AND CRYSTAL-STRUCTURE OF STEREOISOMERS OF 2,5-DIETHOXY-1,4-DIOXANE-2,5-DIMETHANOL, Tetrahedron, 50(33), 1994, pp. 10055-10060
1,3-Dihydroxy-2-propanone (dihydroxyacetone) in aqueous solution is an
equilibrium remeniscent of the one in ketoses. When reacted with trie
thyl orthoformate and ethanol two stable diethyl ethers were isolated
and their structures have been shown to be the cis- and trans-isomers
of 2,5-diethoxy-1,4-dioxane-2,5-dimethanol. NMR spectroscopy and X-ray
crystallography revealed that the trans-isomer adapts chair conformat
ion while the cis-isomer is a twist-boat both in solution and crystall
ine state.