Peracetic acid oxidative ozonolysis

Thermolysis of the methylenecyclobutanone (237) in refluxing 1,2-dichlorobenzene gave a 82 18 mixture of the isomers (238) and (239), with (239) probably being formed from (238). Ozonolysis and peracetic acid oxidation of each of the isomers gave... 

Ozonolysis of 2-styryl-4-methylthiazole followed by oxidation of the intermediate carbonyl compound with peracetic acid yields 4-methyl-2-thiazolecarboxylic acid (30). 

OZONOLYSIS. (1) Oxidation of an organic material, i.e., tall oil, oleic acid, safflower oil, cyclic olefins, carbon treatment, peracetic acid production by means of ozone. (2) The use ol ozone as a tool in analytical chemistry to locate double bonds in organic compounds and a similar use in synthetic organic chemistry for preparing new compounds. Under proper conditions, ozone attaches itself at the double bond of an unsaturated compound to form an ozonide. Since many ozonides are explosive, it is customary to decompose them in solution and deal with the final product. See also Oxygen. 

The cleavage of oleic acid to azelaic acid and pelargonic acid with ozone as oxidant is one of the important industrial applications of ozonolysis [2]. However, finding a catalytic alternative to this unsuitable and hard-to-handle oxidant is in the interests of research groups all over the world. The cleavage of internal C=C double bonds by use of a Re, Mo, or W catalyst with H2O2 as oxidant, or a Ru catalyst with peracetic acid [12], is known. 

Peracetic acid and formaldehyde are the expected ozonolysis products for acetone enol (6), and they are obtained in roughly equimolecular ratio. Infrared spectra cannot be used to identify them since peracetic acid in propan-2-ol absorbs at 1755 cm. , coinciding with a minor solvent peak, while formaldehyde monomer would presumably exist as hemi-acetal. Peracetic acid does not survive gas chromatography at 40 °C. on a polypropylene oxide/glycerol condensate (GPO-50)-glutaric acid phase. However, the peracid titer partitioned between trichlorofluoro-... 

---