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Mechanistic aspects of reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution
Author(s) -
Salin Alexey V.,
Fatkhutdinov Albert R.,
Il'in Anton V.,
Sotov Evgeniy I.,
Sobanov Alexandr A.,
Galkin Vladimir I.,
James Brian R.
Publication year - 2013
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.3154
Subject(s) - chemistry , zwitterion , carbanion , phosphonium , acetic acid , triphenylphosphine , reactivity (psychology) , kinetic isotope effect , alkene , solvent , proton , photochemistry , organic chemistry , medicinal chemistry , computational chemistry , catalysis , deuterium , molecule , medicine , physics , alternative medicine , pathology , quantum mechanics
Kinetic data provide evidence that proton transfer to the carbanion centre of a phosphonium zwitterion is the rate‐determining step in quarternization reactions of triphenylphosphine with electron‐deficient alkenes in acetic acid solution. This conclusion is based on the third‐order rate equation , the reactivity of the alkenes, and solvent isotope effects in deuteroacetic acid. Copyright © 2013 John Wiley & Sons, Ltd.