Physical Sciences and Mathematics Commons^™

The Reaction Of Organoboranes With N-Chloro-N-Sodiocarbamates: A Convenient Synthesis Of N-Alkylcarbamates, Nanette M. Wachter-Jurcsak

Chemistry & Biochemistry Theses & Dissertations

N-alkylcarbamic acid esters are used extensively as fungicides, herbicides and pesticides. Industrial methods of preparation employ highly toxic reagents in their synthesis. Convenient and safe alternative methods are necessary.

Organoboranes are electrophilic compounds which can be employed as a source of alkyl substituents. They have been shown to successfully transfer alkyl groups to the nitrogen of chloramines. N-Alkylation of carbamic acid esters by reacting the corresponding N-chloro-N-sodiocarbamate with a variety of trialkylboranes is described. The yields of the various N-substituted products are discussed.

Two synthetic methods were devised. Originally, an equivalent of the isolated N-chlorocarbamate salt was added to the …