Synthesis and Evaluation of New Intramolecular Cure Intermediates.

The objectives of this research were the synthesis of 1,4,4,7-tetraphenyl-hepta-1,6-diyne-3,5-dione, 1,3,4,6-tetraphenylhexa-3-ene-1,5-diyne, 3-amino-2-m-aminophenylethynyl-N-phenylbenzamide and 4-amino-2-m-aminophenylethynyl-N-phenylbenzamide and their evaluation as potential intramolecular cure IMC agents. The reaction of diphenylmalonyl dichloride with phenylacetylene in the presence of bistriphenylphosphinepalladiumIIdichloride yields diphenylbutadiyne as the major product. The reaction of similarly substituted malonyl dichlorides with cuprous phenylacetylide yields only diphenylbutadiyne. The reaction of phenylethynylmagnesium bromide with substituted malonaldehydes followed by oxidation of the resulting diol to a diketone represents a better synthetic method if the malonaldehydes are available.