An Investigation Directed Toward the Synthesis of Cyclic Polyphenylenes; the Chemistry of 1,3,5-Hexatriene and Its Derivatives; and Reactions of Amines in the Vapor Phase over Alumina

摘要

The results of the synthesis of intermediates which will be utilized in the attempted syntheses of ring polyphenylenes are reported. Experimental procedures were devised and preliminary work accomplished on an 'all-meta-' hexaphenylene, an octaphenylene which contains both meta- and paralinkages, and a quinquephenylene which contains within the same molecule ortho-, meta-, and para- linkages. The possibility of migration of unsaturation through or across a benzene nucleus was examined and tentatively it seems that this phenomena has taken place. The syntheses of the 1-,2-,3-chloro-1, 3,5-hexatrienes were accomplish. The geometrical configuration of the less stable isomer of 1,3,5-hexatriene was established by a stereospecific synthesis. The catalytic deamination reaction which in a rather formal way parallels the dehydration of alcohols was explored. (Author)