Journal of the Chemical Society. Perkin transactions I p. 277 - 281 (1980)
Update date:2022-09-26
Topics:
Collins, Peter M.
Gupta, Paul
Travis, Anthony S.
Solutions of di-O-isopropylidene-β-D-erythro-2,3-hexodiulose-2,6-pyranose (8) in various solvents decarbonylate upon irradiation with u.v. light to give an anomeric mixture of 1,2:3,4-di-O-isopropylidene-D-ribulose (10) and (11), accompanied by variable amounts of the unstable olefin (12) and the aldehyde (13).Compound (13) was found to be a thermal breakdown product from the olefin (12).The photoproduct yields were sensitive to the solvent polarity.The furanose derivatives (10) and (11) were produced with a 1.2:1.0 ratio in 30, 35, and 45percent yields in methyl cyanide, benzene, and n-hexane, respectively.The D-ribulose derivatives (10) and (11) were produced on a preparative scale, isolated free from (12) and (13) by distillation, and hydrolysed to D-ribulose.
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