Synthesis of Masked Glyoxal Monoxime and 1-Hydroxyl-aminoacetaldehyde Derivatives
作者:Eugen Gehrer、Wilhelm Klötzer、Nicolas Singewald、Josef Stadlwieser
DOI:10.1055/s-1987-28029
日期:——
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.
乙醇钠催化偶氮-N,N'-双(2, 2-二乙氧基乙基)-N,N'-二氧化物 (2) 裂解为 1-羟基亚氨基-2 的 E/Z 混合物 (6.5:1),报道了2-二乙氧基乙烷(3a)。肟钠盐的烷基化主要提供烷氧基亚氨基-2,2-二乙氧基乙烷3b-e的E-异构体。相同的化合物也可通过羟胺或O-烷基羟胺与二乙氧基乙醛(4)的反应来制备。用氰基硼氢化钠将肟和O-烷基肟还原成相应的羟胺衍生物5a-e。