The Cyclization of Natural Rubber

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Abstract
The resinification of natural rubber by acid catalysts has been investigated since the beginnings in 1937 of interest in the chemical reactivity of rubber. During the reaction there is a partial loss in unsaturation but no change in the empirical formula of the rubber, C5H8. No general agreement exists on the decrease in unsaturation, values from 40 to 90% of the original having been quoted. (see PDF for diagram) The reduction in the number of double bonds has been attributed to an intramolecular bond formation leading to formation of cyclic structures. D'Ianni, Naples, Marsh, and Zarney have suggested the generally favored structure I, formed by reaction between pairs of adjacent isoprene units of the rubber chain. Van Veersen on the other hand, has proposed the more highly condensed polycyclic structure II. with the cyclization proceeding along the chain to involve a number of adjacent isoprene groups.

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