Amides, azidation

Oxamic Acid Azide (Azido Oxamate, Oxamido-azide, Oxamidsaureazid or Oxalsaure-amid-azid in Ger). H2N.CO.CO.N3, mw 114.02, N 49.11%, OB to C02 —42.09%, crystals from acet+petr eth mp, explds violently ca 115° or on rubbing. Can be prepd by treating the hydrazide of oxamic acid with Na nitrite in w Refs 1) Beil 2, (244) 2) T. Curtius, JPraktChem [2] 91, 426 (1915) 3) Urbanski 3... 

Conversion of Amides to cx-Azido Amides Azidation or Azido-de-hydrogenation... 

Catalytic hydrogenation or LiAlH4 reduction of amides, azides or nitriles produces amines (see Section 5.7.23). 

Reduction of amides, azides and nitriles Preparation of amines... 

Amides, azides and nitriles are reduced to amines by catalytic hydrogenation (H2/Pd—C or H2/Pt—C) as well as metal hydride reduction (LiAlH4). They are less reactive towards the metal hydride reduction, and cannot be reduced by NaBITj. Unlike the LiAlIU reduction of all other carboxylic acid derivatives, which affords 1° alcohols, the LiAlIU reduction of amides, azides and nitriles yields amines. Acid is not used in the work-up step, since amines are basic. Thus, hydrolytic work-up is employed to afford amines. When the nitrile group is reduced, an NH2 and an extra CH2 are introduced into the molecule. 

Car ba my I Azide Carbamoyl Azide or Azidoformam-ide(called CarbaroidsSureazid Azidoameisensaure-amid or Kohlensaure-amid-azid in Ger),... 

Lithium aluminum hydride is a convenient reagent for reduction of nitro compounds, nitriles, amides, azides, and oximes to primary amines. Catalytic hydrogenation works also. Aromatic nitro compounds are reduced best by reaction of a metal and aqueous acid or with ammonium or sodium polysulfides (see Section 23-12B). Reduction of /V-substituted amides leads to secondary amines. 

Phosphorsaure-amid-azid-ester werden auf einfache Weise durch Umsetzung von Phosphorsaure-amid-chlorid-estem mit Natriumazid in Acetonitril in hohen Ausbeuten hergestellt z. B.884 ... 

We have included not only pure nitride materials but also many amides, azides, oxynitrides (but not nitrates and nitrites), nitride chalcogenides, and nitride halides. Specifically excluded are polymeric compounds (e.g. SxNy), cluster compounds (e.g. Sc2C12N), coordination compounds (e.g. [Pd(NS3)2]), ternary azides and amides, as well as ternary interstitial transition-metal nitrides. We have attempted to include all important structures and all type compounds. This review is also unique in that we attempt to evaluate the... 

Alkali-metal azides are prepared by passing nitrous oxide into the molten metal amide. Azides of other metals are made by reacting sodium azide with the corresponding metal or alkyl salts. Whereas alkali-metal azides are inert to shock, the salts of copper, silver. 

Amines are prepared by reduction of nitro compounds, nitriles, amides, azides, enamines, or imines. 

Carhon nucleophiles of pXa 10-20 have heen most studied and often work hest with these substrates (eq 1), hut enamines, cyclopentadiene anions, enolates (eq 2), organotin, -thaUium, -zinc, -aluminum, -lithium, and -zirconiums, as weU as Grignards (eq 3) and horates, also add to r-allylpaUadium complexes. Heteroatom nucleophiles also add successfully these include amines (eq 4), amides, azides, magnesium amides, sulfonamides, alcohols, acids (eq 5), nitrites, sulhnic acids, thiols, phosphines, and phosphites. Limited use of transition metal nucleophiles is also known. ... 

Amides, azides, nitrites, nitrates, nitric acid... 

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