SULFATION OF HYDROXAMIC ACIDS

The reaction of hydroxamic acids with sulfur trioxide-tertiary amine complexesproceeds by O sulfation to give crystalline water-soluble f-ammonium N-acylhydroxylamine-O-sulfonates. The reaction of a solution of any of these salts witha base generates an isocyanate functionin situ. If thebase employed is a primary or secondary amine, urea derivatives are obtained in good yield. Carbamates are formed by the decomposition of the salts with phenoxide ion. Aliphatic isocyanates are prepared in good yield by treatment of the salts with tertiary amine in the presence of an inert solvent. © 1969, American Chemical Society. All rights reserved.