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Boekelheide reaction : ウィキペディア英語版 | Boekelheide reaction
The Boekelheide reaction is a rearrangement of α-picoline-''N''-oxides to hydroxymethylpyridines. It was first discovered in 1954 by Virgil Boekelheide (1919–2003) at the University of Oregon. The reaction is carried out using trifluoroacetic anhydride (TFAA), followed by an hydrolysis step. ==Mechanism== The mechanism of the Boekelheide reaction begins by an acyl transfer from the trifluoroacetic anhydride to the ''N''-oxide oxygen. The α-methyl carbon is then deprotonated by the trifluoroacetate anion. This sets the molecule up for a ()-sigmatropic rearrangement which furnishes the trifluoroacetylated methylpyridine. Hydrolysis of the trifluoroacetate releases the hydroxymethylpyridine.
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