The Preparation of Dibromoamine and its Reaction with Grignard Reagents

Authors

George H. Coleman, State University of IowaFollow
Charles B. Yager, State University of IowaFollow
Harold Soroos, State University of Iowa

Document Type

Research

Abstract

Dibromoamine was prepared by passing dry ammonia into a cold ethereal solution of bromine. The reaction may be represented by the equation: 3 NH₃ + 2 Br₂ → NHBr₂ + 2 NH₄Br. A study of the decomposition rates of the dibromoamine solution at 0° and -72° shows that the product decomposes very rapidly at 0°, but it is relatively stable at the lower temperature. Dibromoamine reacts with Grignard reagents to produce primary amines, secondary amines, ammonia, and nitrogen. The percentage yields of these products obtained in two typical reactions were as follows: for n-butyl magnesium chloride; n-butylamine 7.8 per cent, di-n-butylamine 2.2 per cent, ammonia 79.0 per cent, nitrogen 5.9 per cent; for benzyl magnesium chloride; benzylamine 29.6 per cent, dibenzylamine 5.5 per cent, ammonia 42.8 per cent, nitrogen 4.7 per cent.

Publication Date

1933

Journal Title

Proceedings of the Iowa Academy of Science

Volume

40

Issue

1

First Page

112

Last Page

112

Copyright

©1933 Iowa Academy of Science, Inc.

Language

en

File Format

application/pdf

Recommended Citation

Coleman, George H.; Yager, Charles B.; and Soroos, Harold (1933) "The Preparation of Dibromoamine and its Reaction with Grignard Reagents," Proceedings of the Iowa Academy of Science, 40(1), 112-112.
Available at: https://scholarworks.uni.edu/pias/vol40/iss1/53