New One-Step Synthesis of Isonitriles

Abstract

A new one-step synthesis of isonitriles is described. The starting materials are a primary amine, chloroform, sodium hydride, and the phase-transfer catalyst 15-crown-5 ether, and the solvent is benzene. Five compounds are used to illustrate the features of the new synthesis: 1-adamantyl isocyanide (2a), 2-adamantyl isocyanide (2b), cis-1,8-diisocyano-p-menthane (2c), 2,4,6-trimethylphenyl isocyanide (2d), and trityl isocyanide (2e). The present synthesis is superior to the existing published syntheses because of its yields are good, the by-products are innocuous (H₂ gas and NaCl), and its workup is simple.

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GRAPHICAL ABSTRACT

Keywords:

• 15-Crown-5 ether
• isocyanide
• primary amine
• synthesis