Synthesis and Characterization of 1,2-Disubstituted Cyclobutene Amides: Polymers and Cycloadducts.

Abstract

A series of model diamides were synthesized from mono- and disubstituted 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 23C for N-alkyl and N,N-dialkyl species to 204 C for the N-phenyl model. Relative rates of thermolysis (by DSC) wit maxima from 208-224 C at 10 C/min. were dependent on the number and type of substituents, and intramolecular hydrogen bondings. Thermolysis products were Diels Alder dimers (for N-mono-substituted materials and for bulky tetrasubstituted models) while polymers formed spontaneously for two tetrasubstituted models with at least one methyl group on each nitrogen. Thermal imidization of cycloadducts was possible in some cases with concomitant oxidation to tetrasubstituted aromatic bisimides.

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Document Details

Document Type
Technical Report
Publication Date
Dec 01, 1987
Accession Number
ADA188974

Entities

People

  • Douglas G. Powell
  • Lon J. Mathias

Organizations

  • University of Southern Mississippi

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DTIC Thesaurus Topics

  • Alkenes
  • Butadienes
  • Chemical Shifts
  • Classification
  • Composite Materials
  • Cyclic Hydrocarbons
  • Cyclobutenes
  • Department Of Defense
  • Governments
  • Melting Point
  • Military Research
  • Mississippi
  • Security
  • Thermal Analysis
  • United States
  • United States Government
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Fields of Study

  • Chemistry

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  • Organic Chemistry