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Mechanism of the Reaction of Trialkyl Phosphites with α-Halogenoacetophenones in Alcoholic Solvents

DOI: 10.1039/P29880000127

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 127 - 132 (1988)

Update date:2022-07-29

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Authors:

Petnehazy, ImrePetnehazy, Imre

Keglevich, GyoergyKeglevich, Gyoergy

Toeke, LaszloToeke, Laszlo

Hudson, Harry R.Hudson, Harry R.

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Article abstract of DOI:10.1039/P29880000127

Second-order rate constants and activation parameters have been determined for the reactions of trialkyl phosphites in alcoholic media with α-chloro- or α-bromo-acetophenones having various substituents in the benzene ring (3,4-Me2, 4-Me, H, 4-Cl, and 4-I).Linear Hammett plots are consistent with the involvement of a common first intermediate in the rate-determining stage, leading to the formation of vinyl phosphate, α-hydroxyphosphonate, and acetophenone.The results provide the first kinetic evidence in support of the initial formation of the previously suggested betaine as a common intermediate in alcoholic solution.Further reaction then involves rearrangement to give the vinyloxyphosphonium species (and hence the Perkow product) or protonation followed by dealkylation to give the α-hydroxyphosphonate.Evidence for the possible formation of dehalogenated ketone via solvolysis of the α-hydroxyphosphonium intermediate is also presented.

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Product name:[2-Bromo-1-(4-chloro-phenyl)-1-hydroxy-ethyl]-phosphonic acid diethyl ester

Cas No:113813-58-4

113813-58-4

R&D Labs maybe for 113813-58-4

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