Studies on the Reactivity of 1-Cyano-1-isocyanoalkylphosphonic Acid Esters

Abstract

The reactivity and the synthetic potential of 1-cyano-1-isocyanoalkylphosphonic acid esters 2c,d were investigated. Reaction of 2c with ethyl thiolate gave (ethylthio)(methyl)-4H-imidazole (3). Interestingly, reaction of 2c,d with methoxide led to various products, namely the substituted 4H-imidazole 4 from 2d and compound 5 from 2c, which was formed by addition of methoxide to the isocyano group. Diethylamine as well as bromine add selectively to the isocyano group to form the compounds 6a,b and 7a,b. Contrary to previous findings, n-propylamine reacted in the same manner as secondary amines to form 8.

Key words

phosphorus - nitriles - isocyanides - heterocycles - 4H-imidazoles

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Present address: Merck-Schuchardt, Dr. Theodor Schuchardt & Co., Eduard-Buchner-Str. 14-20, 85662 Hohenbrunn, Germany.