Abstract
When the two conjugated poly-ynes, 1-phenyl-6-methyl- and 1,6-diphenyl-1,3,5-hexatriynes, were irradiated with UVA in deaerated 2,3-dimethyl-2-butene solution, 1:2 photoadducts, 1-(1'-phenylethynyl-2',2',3',3'-tetramethylcyclopr opyl)-2-(l",2",2",3",3"-pentamethylcyclopropyl) acetylene and 1-(1'-phenylethynyl-2',2',3',3'-tetramethylcyclopr opyl)-2-(1"-phenyl-2",2",3",3"-tetramethylcyclopropyl) acetylene, were obtained, respectively. No photoadduct was formed with aerated 2,3-dimethyl-2-butene, or deaerated solutions of dimethyl fumarate, methyl crotonate, dimethyl maleate, and trans-1,2-dichloroethylene. The results suggest that the reactions proceed from the triplet state only with electron rich olefins such as 2,3-dimethyl-2-butene.