Boekelheide reaction

The Boekelheide reaction is a rearrangement of α-picoline-N-oxides to hydroxymethylpyridines. It is named after Virgil Boekelheide who first reported it in 1954.^[1] Originally the reaction was carried out using acetic anhydride, which typically required a period at reflux (~140 °C). The reaction can be performed using trifluoroacetic anhydride (TFAA), which often allows for a room temperature reaction.^[2]

Mechanism

The mechanism of the Boekelheide reaction begins by an acyl transfer from the trifluoroacetic anhydride to the

which furnishes the trifluoroacetylated methylpyridine. Hydrolysis of the trifluoroacetate releases the hydroxymethylpyridine.

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References

1. doi:10.1021/ja01634a026
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2. doi:10.1080/00397919508011399
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