Synthesis and Characterization of 1,2-Cyclobutenedicarboxamides: Thermally Generated Polymers and Diels-Alder Adducts.
Abstract
A series of model diamides were synthesized from mono- and disinstituted amines with the diacid chloride of cyclobutene-1,2-dicarboxylic acid. Yields ranged from 30 to 70%. Melting points of the purified diamides ranged from less than 23 C for N alkyl and N,N dialkyl species to 204 C for the N-phenyl model. Relative rates of thermolysis (by DSC) with maxima from 208-224 C at 10 C/min. were dependent on the number and type of substituents, and on intramolecular hydrogen bonding. Thermolysis products were Diels-Alder dimers for N-mono-substituted materials and for bulky tetrasubstituted models with at least one methyl group on each nitrogen. Thermal imidization of cyclo adducts was possible in some cases with concomitant oxidation to tetrasubstituted aromatic bisimides.
Document Details
- Document Type
- Technical Report
- Publication Date
- Dec 10, 1987
- Accession Number
- ADA188591
Entities
People
- Douglas G. Powell
- Lon J. Mathias
Organizations
- University of Southern Mississippi