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Synthesis 1987; 1987(7): 633-635
DOI: 10.1055/s-1987-28029
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Synthesis of Masked Glyoxal Monoxime and 1-Hydroxyl-aminoacetaldehyde Derivatives

Eugen Gehrer* , Wilhelm Klötzer, Nicolas Singewald, Josef Stadlwieser
  • *Institut für Organische und Pharmazeutische Chemie, Innrain 52a, A-6020 Innsbruck, Austria
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Publication Date:
20 August 2002 (online)

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Sodium ethoxide-catalyzed cleavage of azo-N,N′-bis(2, 2-diethoxyethyl)-N,N′-dioxide (2) to an E/Z-mixture (6.5:1) of 1-hydroxyimino-2,2-diethoxyethane (3a) is reported. Alkylation of the oxime sodium salt provides mainly the E-isomers of the alkyloxyimino-2,2-diethoxyethanes 3b-e. The same compounds are also prepared by the reaction of hydroxylamine or O-alkylhydroxylamines with diethoxyacetaldehyde (4). The oxime and the O-alkyloximes were reduced with sodium cyanoborohydride to the corresponding hydroxylamine derivatives 5a-e.