Dissertation - Open Access
Doctor of Philosophy (PhD)
Several N1-alkyl-N2-(N,N-dialkylamino)carbodiimides, which were found to form dimeric species, were prepared, and the structure of the dimeric species determined. A study of the reaction chemistry of both the monomeric and dimeric carbodiimides led to the conclusion that dimerization occurred via a (π2s + π2a) ground-state, symmetry-allowed mechanism, and that thermal decomposition of the dimeric species occurred via a (π2s +-π2s) excited-state, symmetry-allowed mechanism. Although dialkylphosphoramidates have been shown to be useful intermediates in the preparation of unsaturated organic nitrogen compounds, N-acyl- and N-imino-dialkylphosphorohydrazidates were found to be too unstable, forming trialkylphosphates upon distillation, to be of any synthetic value. The preparation of several difunctional and bis-carbodiimides was attempted, but no products were isolated. Based on the side reaction products isolated from the reaction mixtures, it was concluded that the desired carbodiimides did form, but that they were too unstable to be isolated under the reaction conditions used.
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Number of Pages
South Dakota State University
Plautz, Donald Melvin, "The Chemistry of Some Unusual Carbodiimides" (1971). Electronic Theses and Dissertations. 5279.