Reaction of N-alkyl-N′-(trimethylsilyl)carbodiimides with nitrating agents. The synthesis of N-(tert-butyl)-N′-nitrocarbodiimide

Abstract

Reaction of N-Alk-N′-(trimethylsilyl)carbodiimides (Alk = Me, Bu^t) with nitrating agents (N₂O₅, (NO₂)₂SiF₆) affords alkyl(nitro)cyanamides and N-alkyl-N′-nitrocarbodiimides. The product ratio depends on the reaction conditions. N-(tert-butyl)-N′-nitrocarbodiimide can be obtained in almost pure form. This compound is stable at temperatures below 10 °C. Its structure was confirmed by ¹Н, ¹³C, and ¹⁴N NMR. The reaction of N-(tert-butyl)-N′-nitrocarbodiimide with amines provides a new route to N-alkyl(aryl)-substituted N′-(tert-butyl)-N″-nitroguanidines.