94408-98-7Relevant academic research and scientific papers
Photochemistry of diethynyl sulfides: A cycloaromatization for the formation of five-membered rings
Lewis, Kevin D.,Wenzler, David L.,Matzger, Adam J.
, p. 2195 - 2197 (2003)
(Matrix presented) The first five-membered ring cycloaromatization reaction has been demonstrated. Photoirradiation of bis(phenylethynyl) sulfide in hexanes/1,4-cyclohexadiene produces 3,4-diphenylthiophene through the presumed intermediacy of 2,5-didehydrothiophene. In addition, phenylacetylene is produced in this reaction consistent with competing direct carbon-sulfur cleavage. For reactions in ethanol or 2-propanol production of the thiophene is accompanied by the formation of phenylacetylene and a thionoester of the corresponding alcohol. Thiophene products also result from the irradiation of other diethynyl sulfides.
