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Abstract

The process of producing ethynyl aromatic compounds which are useful as intermediates in the preparation of 3-dimensional carbon-carbon structures for aerospace and military applications and as starting materials in the preparation of organic semi-conductors. The ethynyl aromatic compounds may be any of the classes illustrated in FIGS. 1, 2 and 3 of the drawing. Starting compounds for the process may by any compound from the classes illustrated in FIGS. 4, 5 and 6. The starting compound is reacted in the presence of a Friedel-Crafts catalyst in a suitable solvent with an acyl compound from the class illustrated in FIG. 7 to yield a compound within the classes illustrated in FIGS. 8, 9 and 10. The carbonyl groups in this compound are reduced to yield a corresponding alcohol. Each hydroxy group in the alcohol is converted to an easily eliminatable group, e.g., by reacting it with methane sulfonyl chloride, when subjected to basic conditions. The chlorine and the easily eliminatable groups are then eliminated under basic conditions to yield the desired ethynyl aromatic compound. Illustrative examples of products produced by the process of the invention include 4-4'-diethynyldiphenyl methane; 1,2-(4,4'-diethynyldiphenyl) ethane; 1,1-(4,4'-diethynyldiphenyl) ethane; tris(4-ethynyl phenyl) methane; 4-ethynyl toluene; 2,2'-(4,4'-diethynyldiphenyl) propane; and 4-ethynyl biphenyl.

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First Claim