I-Propylisocyanide

Uses

Isopropyl isocyanide may be used in the preparation of:

• Ugi ligand A2C11I1, which is employed in the solid-phase Ugi synthesis.
• Pentafluorophenyl (PFP) functional monomers, via Passerini reaction.
• Dinuclear copper complex [Cu₂(μ-PiPr₂bipy)₂{μ-CNCH(CH₃)₂}](PF₆)₂ [PiPr₂bipy = 6-(diisopropylphosphanyl)-2,2′-bipyridine].
• (3E)-(Imino)thiaisoindoline 1,1-dioxide derivative.
• N,N′-diisopropylcarbodiimide (DIC) analog via reaction with propan-2-amine.
• 1-t-butyl-2-isopropyldiaziridinone via reaction with 2-methyl-2-nitrosopropane
• isopropyl isocyanate via reaction with ozone
• 1-phthalimidoazetidines via [1+3]cycloaddition reaction with 1-pththalimidoaziridines

Preparation

To a flask containing 100 ml (0.85 mole) of distilled quinoline is added with stirring 41 gm (0.214 mole) of /7-toluenesulfonyl chloride (see Note), and the solution is warmed to 75°C. Then 18.4 gm (0.212 mole) of isopropylformamide is added and the pressure of the system is reduced to 70 mm Hg. The isopropylisonitrile as it forms distills into a liquid nitrogencooled receiver. (Dry ice is not as effective but may be used.) The product is redistilled to afford 4.2 gm (30%), b.p. 88-89°C (735 mm Hg).

General Description

Isopropyl isocyanide is an alkyl isocyanide.