Ozonolysis hydroperoxide synthesis

SCHEME 13. Synthesis of a-alkoxy hydroxy hydroperoxides by ozonolysis, OMe OOH... 

NMR spectroscopy, 694-5 vibrational spectra, 692 X-ray diffraction, 695-6 synthesis, 309-51 tertiary, 690-1 theoretical aspects, 67-84 thymine ozonolysis, 616 see also Chiral hydroperoxides DNA... 

The cleavage of alkenes by ozone, usually to give carbonyl compounds as products, is a reaction which has been widely exploited in synthesis and on which a great deal of mechanistic work has been carried out. Reviews of this chemistry are available.The ozonolysis usually leads to the formation of one of two distinct types of peroxidic product (Scheme 34) the cyclic peroxides (53), which are formed in nonnucleophilic solvents, and acyclic hydroperoxides, such as (54X which are formed in the... 

The ozonolysis of cyclic alkenes in protic solvents followed by reductive decomposition of the hydroperoxides formed is a classical method for dialdehydes synthesis [70], This method is applied for the preparation of 3-ethoxycarbonylglutaric dialdehyde by ozonolysis of ethyl 3-cyclo-pentenecarboxylate. The dialdehyde is an intermediate in the sjmthesis of dolazetrone mesitilate, which is an active medical substance in AN-ZEMET anti-emetik. Zn/AcOH, phosphines, amines and sulfides such as 3, 3 -thiodipropionic acid and its salts are the most suitable redactors for this system. Their efficiency is comparable to that of methyl sulphide but without its shortcomings. The polymer immobilized 3,3 -thiodipropionic acid is also very active in this reduction reaction [70]. 

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