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Isomerization of Aldoximes to Amides under Substantially Neutral Conditions

Isomerization of Aldoximes to Amides under Substantially Neutral Conditions

  1. Gradient
    Abstract: Ten aldoximes were isomerized to amides in good yields, according to the equation RCH=NOH +RCONHa. Reaction was effected by heating the oxime in a solvent with as little as 0.2 mol. yo of nickel acetate tetrahydrate as a catalyst. Gen-erality was demonstrated by applying the reaction to a saturated and to an unsaturated acid-sensitive aliphatic oxime and to aromatic aldoximes; the aromatic oximes could contain electron-donating or -withdrawing substituents, even though cer-tain of these were in the ortho position and others lend sensitivity toward acidic catalysts. The reaction was unsatisfactory only with 2,4-dihydroxybenzaldoxime and with 9-anthraldoxime (which gave the nitrile). Isomerization of aldoximes with small amounts of nickel acetate thus affords a promising means of characterizing oily oximes and of converting aldehydes to amides, under substantially neutral conditions. Isomerization can be effected also with certain other compounds of metals and with nickel.

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