Rearrangements of N-oxides. A novel synthesis of pyridyl carbinols and aldehydes

V Boekelheide, WJ Linn

Index: Boekelheide; Linn Journal of the American Chemical Society, 1954 , vol. 76, p. 1286,1289

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Citation Number: 260

Abstract

In 1947, Katada reported that the reaction of pyridine-N-oxide with acid anhydrides gives 2- pyridone. This rearrangement has now been investigated with alkyl substituted aromatic-?;- oxides and it is shown that with the 2-and 4-alkyl derivatives the products of this reaction are not pyridones but, instead, are the corresponding pyridyl carbinol derivatives. For example, the reaction of 2-picoline-N-oxide with acetic anhydride gives 2-pyridinemethanol acetate ...