The synthesis of alkylamines and dialkylamines via organoboranes

In 1964, H. C. Brown reported that organoboranes react with monochloramine to produce alkylamines in good yield. However, the preparation of the precursor chloramine was cumbersome and tedious.

This reaction was modified such that monochloramine was generated in the presence of the organoborane, eliminating the need of preparation and standardization of ethereal solutions of monochloramine.

This reaction was subsequently extended to the preparation of N-13 and N-15 labeled alkylamines. Such materials are important in biomedical research.

Finally, the reaction of organoboranes with N-chloroalkylamines was investigated. This study culminated in a convenient preparation of dialkylamines.