• Aromatic rings can be aminated in the presence of AlCl3: J. Am. Chem. Soc., 83, 221 (1961). Reaction is more successful with certain heterocycles, N,N'-dimethyluracil giving the 5-amino-derivative almost quantitatively: Tetrahedron Lett., 2751 (1973).
• A one-pot synthesis of aryl or heteroaryl amines from carboxylic acids (as their chlorides) has been reported, equivalent to the Schmidt or Hofmann reactions: Synthesis, 1143 (1990).
• With aqueous NaOH, hydrodeamination of primary amines to alkanes is possible for simple aliphatic amines, amino acids or even peptides: J. Am. Chem. Soc., 100, 341 (1978).
• Aminating agent for nucleophiles. For a review of chemistry, see: Org. Prep. Proced. Int., 14, 265 (1982).
• Primary and secondary amines are converted to hydrazines: J. Org. Chem., 14, 813 (1949); Chem. Ber., 92, 2521 (1959); pyridine to 1-aminopyridinium salts: Org. Synth. Coll., 5, 43 (1977); benzotriazole to the benzyne precursor 1-aminobenzotriazole: J. Chem. Soc., Chem. Commun., 192, 193 (1965); for preparation of the bis(aminotriazolobenzene), a precursor of "1,4-dibenzyne", see: Tetrahedron Lett., 25, 2073 (1984).
• Reaction with ketones results in oxime sulfates which undergo the Beckmann rearrangement to amides on heating: J. Org. Chem. USSR, 17, 2284 (1981); the conversion of cyclic ketones to lactams can conveniently be carried out as a one-step operation: Synthesis, 537 (1979); J. Org. Chem., 54, 4419 (1989); Org. Synth. Coll., 7, 254 (1988).
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Can also provide a source of the reducing agent diimide: Liebigs Ann. Chem., 645, 1 (1962); 721, 240 (1969). For examples of the use of diimide in the reduction of alkenes, see Hydrazine monohydrate, A14005.• Aldehydes are converted directly to nitriles: Tetrahedron Lett., 3187 (1974): Helv. Chim. Acta, 59, 2786 (1976).
Corrosive (C)
