ChemInform Abstract: Regioselective Synthesis of 1-Alkyl-1-phenylhydrazines, 2-Alkyl-1-phenylhydrazines, and 1,2-Dialkyl-1-phenylhydrazines.
Abstract
The hydrazonophosphorane (II), generated by reaction of the hydrazinophosphonium bromide (I) with BuLi, is treated with the alkyl halides (III) to produce the 1-alkyl-2-phenylhydrazines (V) after hydrolysis of the corresponding phosphonium halides (IV).
ChemInform Abstract
The hydrazonophosphorane (II), generated by reaction of the hydrazinophosphonium bromide (I) with BuLi, is treated with the alkyl halides (III) to produce the 1-alkyl-2-phenylhydrazines (V) after hydrolysis of the corresponding phosphonium halides (IV). Lithiation of the intermediate (II) and subsequent coupling with the alkyl halides (III) yields regioselectively the hydrazonophosphoranes (VI), which are hydrolyzed to form the 1-alkyl-1-phenylhydrazines (VII). Coupling of (VI) with the alkyl iodides (VIII) and subsequent hydrolysis give the trisubstituted hydrazines (X).
