EMAIL THIS PAGE TO A FRIEND

Proceedings of the National Academy of Sciences of the United States of America

Vitamin B12S-promoted model rearrangement of methylmalonate to succinate is not a free radical reaction.


PMID 2326276

Abstract

To probe for free radical intermediates in the model methylmalonate to succinate rearrangements promoted by vitamin B12s, 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 bromomethyl-pentenylmalonate 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 B12s, little cyclized product is observed; the major product is the pentenyl succinate. This result demonstrates that the latter rearrangement does not follow a free radical pathway.

Related Materials

Product #

Image

Description

Molecular Formula

Add to Cart

136441
Dimethyl malonate, 98%
C5H8O4
63380
Dimethyl malonate, purum, ≥96.0% (GC)
C5H8O4