Reactions of phosphorus compounds. Part XXII. A reinvestigation of the reactions of activated alkynes with triphenylphosphine hydrobromide. An investigation of the reactions with bases of the vinylphosphonium salts prepared
- 1 January 1970
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- No. 14,p. 1901-1905
- https://doi.org/10.1039/j39700001901
Abstract
The reaction of triphenylphosphine hydrobromide with phenylpropiolic acid (1b) leads not to (Z)-2-carboxy-1-phenylvinyltriphenylphosphonium bromide (3B), as reported, but to a mixture of the E- and Z-isomers (3A and B). These isomeric vinylphosphonium salts can be converted into the corresponding 2-ethoxycarbonyl derivatives (4A and B) by way of the zwitterionic (E)- and (Z)-3-phenyl-3-triphenylphosphonioacrylates (10A and B). The salt (4A) is also formed by treatment of triphenylphosphine hydrobromide with ethyl phenylpropiolate (1c); again in disagreement with the literature report. The reactions of the salts prepared with alkoxides are reported.Keywords
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