Acid-catalyzed hydrolysis of vinyl phosphates and vinyl acetates. The substituent effects of diethyl phosphoryloxy and acetoxy groups
SY Attia, JP Berry, KM Koshy, YK Leung…
Index: Attia,S.Y. et al. Journal of the American Chemical Society, 1977 , vol. 99, p. 3401 - 3408
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Citation Number: 7
Abstract
Abstract: The rates of hydration of diethyl a-substituted vinyl phosphates ((Et0) 2P02CR= CH2, R= H, Me. c-Pr, and EtO) and tu-substituted vinyl acetates (AcOCR= CH2. R= c-Pr and EtO) in aqueous acid at 25" C have been determined. The rates, solvent isotope effects. isotopic labeling studies, and acidity dependence of the rates are consistent with the As~ 2 niechanism of rate-determining protonation on carbon. Electrophilic substituent ...
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