An Investigation of Alternate Synthesis for 2,2' -BIS(Phenylethynyl)-5, 5' -Diaminobenzidine

Abstract

Several routes were investigated to develop an improved lower cost synthesis of the cited tetramine; a critical monomer used in forming the polyphenylquinoxaline polymer system with 2,2'-bis(phenylethynyl) moieties for intramolecular cyclization to the fused dibenzoanthracene structure. An immediate precursor to the tetramine 4-bromo-5-phenylethynyl-0-phenylenediamine was prepared in 43% overall crude yield from 0-nitroamide. Activated coupling through the aryl bromide using the tris-(triphenylphosphine) Ni(0) species was unsuccessful. Substrate chelation of the Ni(0) via the 0-diamine functionality was suggested as an inhibiting mechanism.

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Document Details

Document Type
Technical Report
Publication Date
May 01, 1985
Accession Number
ADA162197

Entities

People

  • Alan A. Shaffer
  • Frederick L. Hedberg
  • Patricia M. Lindley

Organizations

  • Wright Laboratory

Tags

Communities of Interest

  • Ground and Sea Platforms

DTIC Thesaurus Topics

  • Alkenes
  • Amides
  • Chemical Products
  • Chemical Reactants
  • Chemical Reaction Properties
  • Chemical Synthesis
  • Chemistry
  • Composite Materials
  • Materials
  • Materials Laboratories
  • Organic Chemistry
  • Security

Fields of Study

  • Chemistry

Readers

  • Organic Chemistry
  • Polymer Science and Engineering.
  • Polymer Science and Technology