Journal of the Chemical Society. Perkin transactions I p. 1363 - 1366 (1981)
Update date:2022-08-17
Topics:
Szpala, Anthony
Tebby, John C.
Griffiths, D. Vaughan
Dimethyl trans-but-2-enoylphosphonate has been prepared in moderate yield from the reaction of trimethyl phosphite with excess of trans-but-2-enoyl chloride.When the reaction is carried out using equimolar quantities of reactants the major product is the trans-but-2-enoyl ester (5).This ester is formed by the facile reaction of the trans-but-2-enoyl phosphonate with trimethyl phosphite to give the pentacovalent oxaphospholen (6) which is then attacked by trans-but-2-enoyl chloride.The reactions of trialkyl phosphites with 2-methylpropenoyl and propenoyl chlorides follow similar pathways but at different relative rates.
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