Hock cleavage

Fig. 6 Hock cleavage degradation of fatty acids. Reproduced from [33] by permission of Springer...

Ozonolysis has been applied to the oxidative functionalization of triglycerides. Papers and reviews, and a few patents, have been issued on the ozonolysis of seed oils for the production of plastics [95, 96]. Theoretically, the oxidation products that are accessible via ozonolysis of fatty acid esters are the same as those that are isolated from the photo-induced singlet oxygen cleavage of the same substrates, via Hock cleavage [28-33]. The mixture of products that come from the ozonolysis of... 

Hock-cleavage, hpid oxidation, 946 HOI see Hypoiodous acid HomoaUyhc alcohols, transition metal peroxide oxidation, 1089-94... 

After-reactions such as Hock-Cleavage or dehydration may become predominant at room or higher temperatures. While, for example, hydroperoxide 278 is cleaved to two molecules of cyclohexanone (280) only in the presence of acid,206 photosensitized oxygenation of allo-ocimene (281),220 homoverbenene (286),198 sorbic acid methyl ester... 

A fourth, more recent method for generating enols via Hock cleavage of allylic hydroperoxides is discussed in Section 5.4.4.2. 

Aldehyde fragment 1 Hock cleavage of a fatty acid hydroperoxide forming two aldehyde fragments... 

Retention of the chirality of 45-H(P)NE from 135-HPODE was attributed to Hock cleavage of a 10,13-diHPODE [61]. When 10,13-diHPODE was synthesized, however, it was found that this intermediate does not form 4-HPNE under autoxida-tion conditions thus ruling out this mechanistic proposal [62,63]. 

Figure 4.9. Hock cleavage meehanism for the fragmentation of allylie hydroperoxides into two carbonyl products.

The conversion of dihydroartemisinic acid to artemisinin is believed to be a ntMienzymatic spontaneous photooxidation or autoxidation reaction. The mechanism of this complex transformation is shown to involve four steps first, initial reaction of the C11-C12 double bond of dihydroartemisinic acid with single molecular oxygen second is the Hock cleavage of the resulting tertiary allylic... 

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