Ozonides thermolysis

Trioxolanes (57) containing at least one ring hydrogen undergo quantitative thermolysis to give a carboxylic acid and carbonyl derivative (Scheme 8) <89JOC383>. Monosubstituted ozonides (57 ... 

Thermolysis of the 1,2,4-dioxathiolane (65) (a thioozonide) in refluxing /-butylbenzene gave a mixture of the thiolactone (66) (31%) and the ketone (67) (65%) (Equation (6)) <9lJCS(Pl)3043>. The former product is consistent with a thermolytic pathway similar to that observed for ozonides of allylic compounds and of methylene cyclobutanes (see earlier in this section). 

L-xy/o-Hexulosonic acid has been prepared via oxidation of 3,4 5,6-di-0-iso-propylidene-L-sorbose and the racemic derivative (296) was produced on thermolysis of the ozonide (27) (see Chapter 3). 3-Deoxy-D-uw6i/io-[l- C]heptulosonic acid 7-phosphate has been synthesized by addition of potassium [ C]cyanide to 2-deoxy-D-ara6i o-hexose 6-phosphate, hydrolysis, and selective oxidation of the resulting 3-deoxyheptonic acid 7-phosphates at C-2 with potassium chlorate-vanadium(v) oxide. A one-step synthesis of a mixture of 3-deoxy-D-r/6o- and -D-araWno-heptulosonic acid 7-phosphates is based on a metal-ion-catalysed reaction of o-erythrose 4-phosphate with oxalacetate. ... 

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