Reactivity of cyclic and acyclic olefinic hydrocarbons in acid-catalyzed hydration

Chwang, W. K.; Nowlan, Vincent J.; Tidwell, Thomas T.

doi:10.1021/ja00464a024

Cited by 64 publications

(30 citation statements)

References 4 publications

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“…Equation 4 was obtained by mechanistic studies on the acidcatalyzed hydration of alkenes [13,14]. Since the equilibrium constant K, defined in terms of liquid phase concentrations:…”

Section: Resultsmentioning

confidence: 99%

Effect of solvent on the kinetics of the hydration of 2-methylpropene catalyzed by strong acid ion exchangers

Meuldijk

Joosten

Stamhuis

et al. 1989

Journal of Molecular Catalysis

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“…Equation 4 was obtained by mechanistic studies on the acidcatalyzed hydration of alkenes [13,14]. Since the equilibrium constant K, defined in terms of liquid phase concentrations:…”

Section: Resultsmentioning

confidence: 99%

Effect of solvent on the kinetics of the hydration of 2-methylpropene catalyzed by strong acid ion exchangers

Meuldijk

Joosten

Stamhuis

et al. 1989

Journal of Molecular Catalysis

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“…as derived from mechanistic studies on the acid-catalyzed hydration of alkenes [6,7]. In the absence of mass transfer limitations, the alkene concentration in eqn.…”

Section: Rate Constantsmentioning

confidence: 99%

Effect of solvent on the hydration of 2-methyl-propene in solutions of p-toluenesulfonic acid and poly(styrenesulfonic acid)

Meuldijk

Joosten

Stamhuis

1986

Journal of Molecular Catalysis

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“…[2]) and the known hydrogen ion concentrations of the buffers. These results are also listed in Table 3.…”

Section: Resultsmentioning

confidence: 99%

Acid-catalyzed hydrolysis of tetramethoxyethene in aqueous solution. Initial state stabilization by the methoxy groups

Kresge¹,

Leibovitch²,

Kopecky³

1990

Can. J. Chem.

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The acid-catalyzed hydrolysis of tetrarnethoxyethene to methyl dirnethoxyacetate in aqueous solution at 25OC was found to occur with the hydronium-ion catalytic coefficient kH+ = 0.454 M-' s-I, to give the solvent isotope effect k H -/ k D -= 3.15, and to provide a Bronsted relation based upon six carboxylic acids with the exponent a = 0.42. These data indicate that the reaction proceeds via rate-determining proton transfer from the catalyzing acid to an olefinic carbon atom of the substrate. They also show tetramethoxyethene to be 1.0 X lo6 times less reactive than 1,l-dirnethoxyethene (ketene dirnethyl acetal), a rate retardation 600 times greater than that expected from initial state stabilization by the two additional rnethoxy groups in tetramethoxyethene; possible causes of this disparity are discussed. On a trouve que l'hydrolyse acido-catalysee du tCtrarntthoxyCthene en dimethoxyacttate de rntthyle, en solution aqueuse, a 25"C, se produit avec un coefficient catalytique de l'ion hydronium kH+ = 0,454 M-' s-' et un effet isotopique du solvant k H + / k D + = 3,15 et qu'elle dome lieu a une relation de Bronsted, basCe sur six acides carboxyliques, avec un exposant a = 0,42.Ces donntes indiquent que la rtaction se produit par le biais d'un transfert de proton du catalyseur acide avec un atorne de carbone olCfique et que ce transfert limite la vitesse de la rtaction. Ces donnCes dtrnontrent aussi que le t6tramtthoxyCthtneest 1,O X lo6 fois rnoins rtactif que le 1,l-dirnCthoxyCthkne (dimethyl acCtal du cCttne); ce ralentissernent est 600 fois plus grand que celui attendu sur la base d'une stabilisation de 1'Ctat initial du tCtrarnCthoxyCthkne par deux groupernents rnCthoxyles additionnels: on discute des causes possibles de cette disparitC.Mots clis: tCtrarnCthoxytthtne, rCactivitC de la double liaison carbone-carbone, acttal du cCttne, hydrolyse de 1'Cther vinylique.[Traduit par la revue] Introduction Alkoxy substituents raise the reactivity of carbon-carbon double bonds to electrophilic addition by impressively large amounts. Methyl vinyl ether (I), 2, for example, is protonated on carbon fifteen orders of magnitude more rapidly than is ethylene ( 2 ) , 1, and ketene dimethyl acetal, 3, is another five orders of

show abstract

Reactivity of cyclic and acyclic olefinic hydrocarbons in acid-catalyzed hydration

Cited by 64 publications

References 4 publications

Effect of solvent on the kinetics of the hydration of 2-methylpropene catalyzed by strong acid ion exchangers

Effect of solvent on the kinetics of the hydration of 2-methylpropene catalyzed by strong acid ion exchangers

Effect of solvent on the hydration of 2-methyl-propene in solutions of p-toluenesulfonic acid and poly(styrenesulfonic acid)

Acid-catalyzed hydrolysis of tetramethoxyethene in aqueous solution. Initial state stabilization by the methoxy groups

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