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. 1978;5(Suppl 1):s227–s230. doi: 10.1093/nar/1.suppl_1.s227

Beckmann rearrangement of nucleoside-5-oxime

D Bärwolff 1, P Langen 1
PMCID: PMC6581401

Abstract

The oxime of 5-formyl-2′-deoxyuridine (I) can be dehydrated by acetic anhydride to give 5-cyano-2′-deoxyuridine (II). In the HBr/acetic acid/acetic anhydride mixture I becomes rearranged to 5-N-acetamido-2-deoxyuridine (III).

The pathway of this unexpected reaction is investigated.

Articles from Nucleic Acids Research are provided here courtesy of Oxford University Press

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