It has been proposed that the mechanism of the ozonolysis of 1-decene proceeds via a 1,3-dipolar cycloaddition of ozone to the alkene. The resulting primary ozonide then fragments to give nonanal oxide and formaldehyde. This molecular pair, within the same solvent cage, reorganizes and undergoes another concerted cycloaddition to give rise to the secondary ozonide, which can be isolated from the reaction mixture by simple workup. Specific interactions of N,N-dimethylformamide (DMF) and alcohols with the carbonyl oxide formed during ozonolysis give rise to isolable products that indicate how this mechanism occurs. The details of the mechanism will be discussed.
