
%0 Journal Article
%A Meisters, A 
%A Swan, JM 
%T Organophosphorus compounds. IV. The reaction of Alk-1-ynes with phosphorus pentachloride, and a new route to Alka-1,2-dienes
%J Australian Journal of Chemistry
%D 1965/02/01
%V 18
%N 2
%P 155-162
%K 
%R https://doi.org/10.1071/CH9650155
%U https://www.publish.csiro.au/paper/CH9650155 
%X The addition of phosphorus pentachloride to four representative linear alk-1-ynes is accompanied by an allylic shift of a hydrogen atom. Hydrolysis of the resulting complexes yields 2-chloroalk-2-enylphosphonic acids rather than 2-chloroalk-1-enylphosphonic acids as reported in the literature. The 2-chloroalk-2-enylphosphonic acids undergo fragmentation in hot alkali yielding 1,2-alkadienes, chloride, and phosphate ions. The sequence alk-1-yne &#8594; 2-chloroalk-2-enylphosphonic acid &#8594; l,2-alkadiene constitutes a new and mild method for effecting this isomerization. 
