Oxidation Ozonolysis

Cleavage of an alkenoic acid can be carried out with permanganate, a permanganate—periodate mixture, periodate or with nitric acid, dichromate, ozone, or, if the unsaturation is first converted to a dihydroxy compound, lead tetraacetate (71,73). Oxidative ozonolysis is a process for the manufacture of azelaic acid [123-99-9] and pelargonic acid (74). 

SCHEME 20. Application of oxidative ozonolysis for structural analysis of unsaturated fatty acid hydroperoxides... 

Carbenes, dioxirane preparation, 1132 Carbocations, antimalarial endoperoxides, 1309 Carbohydrate hydroperoxides, Mo-catalyzed olefin epoxidation, 432, 436 Carbohydrates, TBARS assay, 669 Carbonate esters, oxidative ozonolysis, 737, 738... 

Menthyl chlorofornate, oxidative ozonolysis, I il, 738 Metabolism, up/downregulation, 610 Metal-catalyzed reactions... 

Oxidative ozonolysis, analytical methods, 737 Oxidative stress... 

Michaelis-Arbnzov Reactions Phosphonomethylation Michael Addition Anionic Formylation Oxidation Ozonolysis Rednction... 

Thermal and Anionic Phosphonylation Phosphonomethylation Michael Addition Electrophilic Snbstitntion Heck Conpling Diels-Alder Reactions Oxidation Ozonolysis... 

Although the structure and relative stereochemistry were easily determined by classical degradative and, later, synthetic studies, the absolute stereochemistry of the two enantiomers proved more challenging. Oxidative ozonolysis of (-i-)-ipomeamarone afforded a lactone, [a]o +7.4° (39), which had similar rotation to the same lactone (42) ([a]o +6.3°) prepared from / -linalool (43) (In this work (39) the sign of the optical rotation quoted was wrong, because, as determined later, the lactone prepared in this way has a negative rotation). On this basis, C-4 of (+)-ipomeamarone was... 

CHEMICAL MODIFICATION The following chemical modifications of cis-1,4-polyisoprene are employed as a convenient way of altering physical and mechanical properties hydrohalogenation, halogenation, oxidation, ozonolysis, hydrogenation, carbene addition, cyclization. ... 

If our labeled linoleic acid is transformed only into acids of the linoleic acid type, the only radioactive aldehyde obtain by reductive ozonolysis of the liver polyenoic acid mixture will be hexanal. Transformation into the oleic acid type would be indicated by radioactive nonanal, and transformation into the hnolenic acid type by radioactive malonic acid after oxidative ozonolysis. 

---