
TY  - JOUR
A1  - Meisters, A 
A1  - Swan, JM 
T1  - Organophosphorus compounds. IV. The reaction of Alk-1-ynes with phosphorus pentachloride, and a new route to Alka-1,2-dienes
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1965
VL  - 18
IS  - 2
SP  - 155
EP  - 162
KW  - 
UR  - https://doi.org/10.1071/CH9650155 
N2  - 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. 
ER  -

