Abstract
Condensation of D-arabinose dialkyl dithioacetals with cyclohexanone in the presence of zinc chloride gives 4,5- O-cyclohexylidene derivatives for which structures have been established by conversion of the diethyl dithioacetal into the known 2,3-di- O-acetyl- D-arabinose diethyl dithioacetal, and by chromatographic identification of the fragments resulting from oxidation with lead tetra-acetate. By using sulphuric acid-copper sulphate as condensing agent, the principal product is the 2,3:4,5-di- O-cyclohexylidene- D-arabinose dialkyl dithioacetal, which, with warm acetic acid, yields the 2,3- O-cyclohexylidene- D-arabinose dialkyl dithioacetal. Structural assignments for these compounds follow from the oxidation of the dimethyl dithioacetal with lead tetra-acetate in benzene which gives formaldehyde and 2,3- O-cyclohexylidene- D- threo-dihydroxysuccindialdehyde 1-(dimethyl dithioacetal). The latter compound was converted into the known bis(dimethyl dithioacetal) of D- threo-dihydroxysuccindialdehyde.
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