Ozonolysis reaction with cycloalkenes

A similar mechanism has been postulated for reactions involving cycloalkenes. It has been shown that a copolymer of cyclooctene and cyclopentene (labelled on its double bond with is predominantly labelled in the C5 fragment, this result being obtained by reductive ozonolysis of the polymer [9j. The radioactivity found in the C5 diol proves that ring opening polymerization also proceeds via scission on the double bonds rather than cleavage of carbon—carbon single bonds. 

Now we must find a way to convert the starting cycloalkene into the diol shown above. This can be achieved in just two steps. First, the ring is opened with an ozonolysis reaction to produce a dialdehyde. Then, the dialdehyde is reduced to a diol upon treatment with two equivalents of a reducing agent. Acetal formation then gives the final product. 

The yield of OH radicals in the ozonolysis of a number of cycloalkenes has been determined by scavenging OH with cyclohexane (Sidebottom). The derived OH yield of about 40 % was found to be similar to that of cw-2-butene, providing support for the suggestion that OH yields from ozone-alkene reactions depend... 

The cycloalkenes ozonolysis in the presence of methyl pymvate results in tri-substituted ozonides formation. The latter contain three reaction centers (peroxides, proton on the ozonides cycle and methoxy-carbonyl group) accessible for various functionalization. The cyclohexene ozonolysis in the presence of methylpyrovate gives ozonide whose treatment with PPhj or EtjN yields CHO(CHj) CHO and CHO(CH3),COOMe (after esterification), respectively. This method proved to be very convenient and practical way for the synthesis of linear compounds containing various ter-... 

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