Date of Award
Spring 1990
Document Type
Thesis
Degree Name
Master of Science (MS)
Department
Chemistry & Biochemistry
Program/Concentration
Chemistry
Committee Director
Frank E. Scully, Jr.
Committee Member
Roy L. Williams
Committee Member
Charles Bell
Call Number for Print
Special Collections LD4331.C45W33
Abstract
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.
Rights
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DOI
10.25777/115j-8z71
Recommended Citation
Wachter-Jurcsak, Nanette M..
"The Reaction of Organoboranes with N-Chloro-N-Sodiocarbamates: A Convenient Synthesis of N-Alkylcarbamates"
(1990). Master of Science (MS), Thesis, Chemistry & Biochemistry, Old Dominion University, DOI: 10.25777/115j-8z71
https://digitalcommons.odu.edu/chemistry_etds/142