Stannous chloride ketoximes

Generally primary nitro compounds are reduced to aldoximes and secondary to ketoximes by metal salts. On reduction with stannous chloride 1,5-... 

Reduction of cyclohexanone oxime with lithium aluminum hydride in tetra-hydrofuran gave cyclohexylamine in 71% yield [809], and reduction of ketoximes with sodium in methanol and liquid ammonia [945] or in boiling ethanol [946] afforded alkyl amines, usually in good to high yields. Stannous chloride in hydrochloric acid at 60° reduced the dioxime of 9,10-phenanthra-... 

In most cases, the crude imino chloride is treated directly by adding it to a solution of stannous chloride saturated with dry hydrogen chloride the aldehyde is then liberated by steam distillation. The procedure is illustrated by the synthesis of o-tolualdehyde (70%). Imino chlorides have also been prepared by treatment of ketoximes with phosphorus penta-chloride, viz., RR C NOH — RCC1=NR, in preparations of benzalde-hyde and p-chlorobenzaldehyde (70-85%). As in the Stephen reaction (method 164), groups ortho to the imino chloride group hinder the reaction. 

Microwave-assisted Beckmann rearrangement of ketoximes was investigated using stannous (II) chloride in ionic liquid as an efficient catalyst (Niralwad et al, 2011). They carried out conversion of keto halides to lactams by means of sequential azidation and intramolecular Schmidt reaction in a combined flow format. 

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See also in sourсe #XX -- [ , ]

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