Benzyl isocyanide

Chemical Properties

clear colorless to yellowish liquid

Uses

Benzyl Isocyanide is used in the preparation of arylamide compounds. also used as a catalyst in the cycloaddition of norbornenes with internal and terminal acetylenes.

Application

Benzyl isocyanide forms phosphaalkene-containing complexes. Benzyl isocyanide was used in the synthesis of Ru(II) complexes containing hydrazine and benzyl isocyanide ligands. It was used in a three-component coupling process leading to O- and N-arylamides.

Synthesis

Synthesis of benzyl isocyanide
In a 500-mL, round-bottomed flask equipped with a magnetic stirring bar and a pressure-equalizing funnel are placed 5-benzylaminotetrazole (10.5 g, 60 mmol), 100 mL of 10% sodium hydroxide solution, and 70 mL of dichloromethane. The mixture is cooled to 0°C and a solution of NaOBr in water (165 mL, 65 mmol) (Note 2) is added with vigorous stirring over a 15-min period (Note 3). The dichloromethane layer is separated and the aqueous phase extracted with five 50-mL portions of dichloromethane. The combined dichloromethane extracts are dried over anhydrous MgSO4, the drying agent is removed by filtration, and the dichloromethane is removed by simple distillation. The pressure is then reduced to ~20 mm with an aspirator and benzyl isocyanide is distilled at 98–100°C; yield: 5.91 g (84%) (Note 4) and (Note 5).
Organic Syntheses, Coll. Vol. 7, p. 27, 1990
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