Dicyclopentadiene oxidative cleavage

A typical procedure is provided by the oxidative cleavage of endo-dicyclopentadiene to the corresponding dialdehyde (Scheme 1). A solution of potassium permanganate (3.41 mmol) and tri-ethylbenzylammonium chloride (141 mmol) in dichloromethane (40 mL) was added dropwise to a solution of en o-dicyclopentadiene (2.27 mmol) in 20 mL of the same solvent maintained at 0-3 C. After the addition, which took 40-50 min, stirring was continued for an additional 30-40 min by which... 

The first structure type to be established for a hexadiene radical cation was one in which cleavage is achieved without bonding, i.e. a representative of the dissociative mechanism. Dicyclopentadiene and several derivatives can be oxidized to radical cations (137) in which one of the bonds linking the monomer units is cleaved. The unique spin density distribution of 137 is reflected in an unmistakable polarization pattern [386-389]. 

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