Australian Journal of Chemistry

Organophosphorus compounds. IV. The reaction of Alk-1-ynes with phosphorus pentachloride, and a new route to Alka-1, 2-dienes

A Meisters, JM Swan

Index: Meisters,A.; Swan,J.M. Australian Journal of Chemistry, 1965 , vol. 18, p. 155 - 162

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Citation Number: 14

Abstract

Abstract 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- ...

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