Document Type

Dissertation - Open Access

Award Date

1971

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

Abstract

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.

Library of Congress Subject Headings

Carbodimiides

Format

application/pdf

Number of Pages

114

Publisher

South Dakota State University

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