Ozonolysis investigating fragmentation

A very important point to remember when using ozonolysis for structural investigation of polyenes is that the transoid bond is attacked preferentially34. Hence, the advantage of the ozonolysis in polymeric matter is obvious the fragments formed are easier to analyse and they are also indicative of the double-bond positions (see Schemes 1 and 2). 

The influence of structure and temperature upon oxidation selectivity on a methyl group was investigated. A mechanism has been proposed.158 7,7-Dimethyl-2-methylenenorbornan-l-ol undergoes an anomalous ozonolysis to yield a mixture of a rearranged /i-hydroxy ketone and a fragmented carboxylic acid.159... 

Either direction of cleavage of the primary ozonide from a-pinene would produce a carbonyl oxide with ten carbon atoms. Fragmentation of this intermediate might well lead to a number of hydroperoxides we could detect, but only MHP was observed from gas-phase ozonolysis. As in the case of isoprene, neutralisation of the sample from aqueous ozonolysis before analysis indicates that significant amounts of HAHPs are formed in water. These are still under investigation. 

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