The Preparation and Molecular Size of Isorubber Nitrone. (8th Communication)

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Abstract
Continuing earlier experiments of Angeli, Alessandri, and Pegna, of Alessandri and of Bruni, the latter and Geiger have recently studied the action of aromatic nitroso compounds on rubber, and have obtained notable results. The earlier experimentors succeeded only in obtaining from nitrosobenzene a compound of the composition C58H61N5O9. It has recently been proved that one molecule of the nitroso compound for each isoprene nucleus enters the rubber molecule. However, as the earlier investigators have shown, three molecules of nitroso compound react with each C5H8 group when the rubber is warmed in benzene on a water bath for 15 minutes. The solution changes from green to dirty green and finally to brown-red. After cooling it is poured into petroleum-ether, whereupon yellow flakes of the composition [C11H11ON]x, decomposing at 135–140°, separate, the yield being 94–98%. This product is evidently formed by the reaction of one molecule of nitrosobenzene with C5H8 with loss of 2 atoms of hydrogen. This hydrogen reduces a second molecule of nitrosobenzene to phenylhydroxylamine, which with a third molecule yields azoxybenzene. The latter was isolated from the mother liquor. The rubber derivative which is formed may be regarded as a nitrone of an isorubber:

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