DIHYDROXYACETONE DIMERS - SOLUTION AND CRYSTAL-STRUCTURE OF STEREOISOMERS OF 2,5-DIETHOXY-1,4-DIOXANE-2,5-DIMETHANOL

Authors
WAAGEN V BARUA TK ANTHONSEN HW HANSEN LK FOSSLI DJ HOUGH E ANTHONSEN T
Citation
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
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
50
Issue
33
Year of publication
1994
Pages
10055 - 10060
Database
ISI
SICI code
0040-4020(1994)50:33<10055:DD-SAC>2.0.ZU;2-7
Abstract
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.