Synthesis of Monomers for the Preparation of Regiospecifically Substituted Poly(Phenylacetylenes) as Potential Chemical Detectors

• Main Authors: Wentworth,S E, Libby,J B, Bergquist,P R
• Format: Report
• Language: English
• Subjects: ACETIC ANHYDRIDE; ASH84; BROMINATION; CHEMICAL AGENT DETECTORS; Chemical, Biological and Radiological Warfare; CINNAMIC ACID; FLUORINE COMPOUNDS; MONOMERS; NITROGEN COMPOUNDS; Organic Chemistry; PE62105A; Poly(Phenylacetylenes); Regiospecific substituents; SUBSTITUTION REACTIONS; SYNTHESIS(CHEMISTRY)

A number of substituted phenylacetylenes have been prepared as precursors to poly(phenylacetylenes) having regiospecific substitution. These latter were required for a study attempting to correlate structure with electronic properties, especially conductivity. The following phenylacetylenes were prepared: o-, m-, and p-nitrophenylacetylene, p-trifluoromethylphenylacetylene, o-and p-aminophenylacetylene (m-commercially available), o-, m-, and p-acetamido, and m- and p-trifluoroacetamidophenylacetylene. Starting materials were the appropriate nitro or trifluoromethyl cinnamic acids. Bromination followed by dehydrobromination and decarboxylation gave the corresponding phenylacetylenes. The amino compounds were obtained by Zn/NH4OH reduction of the o- and p-nitrophenyl-acetylenes. Acylations were accomplished with acetic or trifluoroacetic anhydride. (Author) Presented at Mid-Atlantic Regional Meeting, Americal Chemical Society, White Haven, PA Apr 83.