
%0 Journal Article
%A Wailer, PC 
%T The condensation of acetylenes with deoxyanisoin
%J Australian Journal of Chemistry
%D 1956/09/01
%V 9
%N 3
%P 373-381
%K 
%R https://doi.org/10.1071/CH9560373
%U https://www.publish.csiro.au/paper/CH9560373 
%X Although deoxyanisoin underwent fission on attempted reaction with sodium or lithium acetylide in liquid ammonia, it condensed normally with 1-hexyne and propyne via the Grignard reagent, the intermediate aoetylenic carbinols dehydrating on distillation. The reaction of acetylenedimagnesium bromide and deoxyanisoin at room temperature afforded the stable 1,2-di-(p-methoxyphenyl)but-3-yn-2-ol, whereas the same reagents under more vigorous conditions resulted in cyclization to 2-methoxy-6-p-methoxyphenylnaphthalene, synthesized from anisil or deoxyanisoin by a Reformatsky reaction via the tetralone. 
