Date of Award

Spring 1990

Document Type


Degree Name

Master of Science (MS)


Chemistry & Biochemistry



Committee Director

Frank E. Scully, Jr.

Committee Member

Roy L. Williams

Committee Member

Charles Bell

Call Number for Print

Special Collections LD4331.C45W33


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 trialkylborane. A convenient alternative to this method avoids the isolation of the N-chloro-N-sodiocarbamate. Six different N-alkylcarbamates were synthesized in yields ranging from 46'k to 100/o. Steric effects of the alkyl substituents have been noted and are discussed.


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