Abstract
AbstractPhotochemical hydrogen peroxide catalyzed degradation of both natural rubber and synthetic cis‐polyisoprene is shown to result in the formation of a low‐molecular‐weight oil functionalised with hydroxyl, carbonyl and epoxide groups. Interestingly, the epoxide groups are shown to be of a trans‐configuration. A scheme is proposed to account for the formation of trans‐epoxide as well as concomitant mainchain isomerization. The preferential formation of trans‐epoxide in free radical oxidations strongly suggests that the naturally occurring cis‐epoxide, present in natural rubber, is due to a stereospecific enzymatic process, and is not the byproduct of radical oxidation.
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