1960
DOI: 10.1021/ja01508a031
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II. Rates of Solvolysis of Triphenylmethyl Acetate and Flouride1—3

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1963
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Cited by 22 publications
(12 citation statements)
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“…As only few investigations of trityl solvolyses had been reported in the past, we have recently performed a systematic investigation of solvolysis reactions of trityl halides and carboxylates . By using stopped‐flow techniques, a method that had not commonly been employed for studying ionization rates, we were able to significantly extend the accessible reactivity range into the millisecond time scale and gain important new insights in rate–equilibrium relationships and the interpretation of linear free energy relationships in general .…”
Section: Introductionmentioning
confidence: 99%
“…As only few investigations of trityl solvolyses had been reported in the past, we have recently performed a systematic investigation of solvolysis reactions of trityl halides and carboxylates . By using stopped‐flow techniques, a method that had not commonly been employed for studying ionization rates, we were able to significantly extend the accessible reactivity range into the millisecond time scale and gain important new insights in rate–equilibrium relationships and the interpretation of linear free energy relationships in general .…”
Section: Introductionmentioning
confidence: 99%
“…Swain and co-workers determined solvolysis rates of trityl acetate in aqueous alcohols and acetone at 25 8C. [9] Bunton Abstract: Ionization rates of para-substituted triphenylmethyl (trityl) acetates, benzoates, and para-nitrobenzoates have been determined in aqueous acetonitrile and aqueous acetone at 25 8C. Conventional and stoppedflow techniques have been used to evaluate rate constants ranging from 1.38 10 À5 to 2.15 10 2 s À1 by conductimetry and photospectrometry methods.…”
Section: Introductionmentioning
confidence: 99%
“…Swain and co‐workers determined solvolysis rates of trityl acetate in aqueous alcohols and acetone at 25 °C 9. Bunton proved that the alkyl–oxygen bond (rather than the acyl–oxygen bond) is cleaved in the rate‐determining step during the hydrolysis of trityl acetate 10.…”
Section: Introductionmentioning
confidence: 99%
“…The resistance of alkyl fluorides to displacement under alkaline conditions has been noted for many years (2)(3)(4)(5)12). In ethanolic sodium ethoxide primary alkyl fluorides undergo mainly substitution at rates which are lo3-lo4 times slower than the corresponding bromides (5).…”
Section: Discussionmentioning
confidence: 99%
“…With respect to alkyl fluorides, however, several workers (3,6,(12)(13)(14) have discovered enhanced rates in the presence of acid. Berstein and Miller (4) observed that the rate of reaction of substituted benzyl fluorides in 70% aqueous ethanol containing various concentrations of hydrochloric acid was dependent on the initial concentration of acid.…”
Section: Discussionmentioning
confidence: 99%