Methyl exchange on silicon during the addition of methylmagnesium iodide to a cyanohydrin O-silyl ether

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Cécile Arbez-Gindre, Valérie Berl and Jean-Pierre Lepoittevin


Abstract

Reaction of [13C]methylmagnesium iodide (99 atom% 13C) with cyanohydrin O-trimethylsilyl ether 1, followed by acidic hydrolysis, led to the formation of a methyl ketone derivative 2a that was only partially labelled (60 ± 5 atom% 13C); this loss of labelling occurred through a methyl exchange reaction on silicon as shown by the presence on intermediate 2b of [13C]methyl groups on silicon (30 atom% 13C).


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