
%0 Journal Article
%A Teitei, T 
%A Collin, PJ 
%A Sasse, WHF 
%T Photochemical syntheses. V. The photo-addition of heterocyclic diarylacetylenes to naphthalene and 1-methylnaphthalene
%J Australian Journal of Chemistry
%D 1972/01/01
%V 25
%N 1
%P 171-182
%K 
%R https://doi.org/10.1071/CH9720171
%U https://www.publish.csiro.au/paper/CH9720171 
%X Eight heterocyclic diarylacetylenes derived from pyridine, furan, thiophen, and thiazole have been irradiated in the presence of naphthalene. Phenyl(4-pyridyl)- acetylene gave the compounds (2a) and (2b), phenyl(3-pyridyl)acetylene gave the compounds (3a) and (3b), and phenyl(2-pyridyl)acetylene compounds (4a) and (4b). From 1-methylnaphthalene and phenyl(3-pyridyl)acetylene the adducts (5a) and (5b) have been isolated and two adducts which formed by addition to the unsubstituted ring were detected. From phenyl(2-thiazolyl)acetylene and naphthalene probably only one isomeric adduct (6b) was isolated. The methiodides of all the new adducts except (6b) have been prepared. The structures proposed for these photo-adducts are based on their p.m.r., mass, and ultraviolet absorption spectra. Factors influencing the isomer distribution and overall yields are discussed in terms of a mechanism previously proposed for the addition of diphenylacetylene to naphthalene. 
