Amines TV-oxides

Tertiary amine TV-oxides are rapidly deoxygenated by carbon disulphide1112. Oximes are reduced to primary amines by titanium(III) chloride in the presence of sodium cyanoborohydride, NaBTpCN1. The combined action of sodium borohydride and a chiral... 

The majority of the complexes are decomposed by water through ligand displacement, although they are not necessarily sensitive to atmospheric moisture. They are generally prepared by direct addition of the amine TV -oxide to solutions of metal salts in organic solvents. Triethyl orthoformate or 2,2 -dimethoxypropane have often been added to the reaction media as desiccants. 

The Meisenheimer rearrangement of / r/-amine TV-oxides (e.g., 185) has been applied to the synthesis of monocyclic 1,2-oxazepines, e.g., 186 (Scheme 91) <1984CPB4117>. 

The rate-determining step in catalytic osmylations is usually the oxidation of the osmium(VI) esters 2 or 735t 37. Depending on the steric requirements of the alkene precursor, the trioxo(l,2-diolato)osmate(VIII) 4, formed in the amine TV-oxide promoted catalytic osmylation, can be further transformed following two different pathways. 

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