Alcohols ozone adducts

Anthryl ethers afford protection to alcohol functions treatment of the derivative with singlet oxygen, generated via the triphenyl phosphite-ozone adduct, followed by mild catalytic reduction, effects regeneration of the free alcohol (Scheme 136). 

Vitamin D2 reacted with maleic anhydride to give a mono Diels-Alder adduct, which hydrolyzed to yield a dicarboxyhc acid. Acetylation of the alcohols, esterification of carboxyHc acids, and hydrogenation gave a compound that, when ozonized, gave a saturated ketone, This molecule... 

Oxetanocin was obtained by carrying out the reaction between 2-methylfuran and benzoyloxyacetaldehyde. The corresponding adduct was treated with ozone, and the product was reduced with NaBPLj. The obtained alcohols were protected. 

When the solvent is or contains an alcohol, it is often incorporated in the ozonation products For example, Kratzl et al (1976) obtained about one mole of ethyl formate per mole of veratrole ozonized when the solvent was 10% ethanol in chloroform Tanahashi et al (1975) obtained methyl esters and, on hydrogenolysis of some ozomde/methanol adducts, methyl benzyl ethers using... 

The resin-bound chiral auxiliary 84 was allowed to react with different vinyllith-ium reagents. The resulting alcohols 85 were treated with n-BuLi, methyl chloro-formate and different cuprate reagents. Finally, the a-alkylated adducts 86 were liberated from the polymer with ozone followed by one of three different workup conditions to provide a primary alcohol, an aldehyde or a carboxylic acid (Scheme 12.32). 

The results of a recent investigational of model systems provide compelling evidence that stabilized atomic oxygen is present in Compound I and Compound II of horseradish peroxidase and the reactive form of cytochrome P-450. Thus, the combination of tetrakis(2,6-dichlorophenyl)-porphinato iron(III) perchlorate (1, Scheme 1) with pentafluoro-iodoso-benzene, m-chloroperbenzoic acid, or ozone in acetonitrile at -35 C yields a green porphyrin-oxene adduct (2). This species, which has been characterized by spectroscopic, magnetic and electrochemical methods, cleanly and stereospecifically epoxidizes olefins (>99% exo-norbornene-oxide), oxidizes alcohols to aldehydes, oxidatively cleaves diols, and demethylates dimethyl aniline (Scheme 1). 

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