To probe for free radical intermediates in the model methylmalonate to succinate rearrangements promoted by vitamin B12., a model series with a pentenyl side chain radical trap has been devised. The control free radical, generated by tri-n-butyltin hydride treatment of bromomethylpentenylmalonate thioester, undergoes rapid cyclization to the six-membered ring, and, as anticipated, no succinate rearrangement product is detected. By contrast when the bromide is treated with vitamin B12., little cyclized product is observed;
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