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Retentive Solvolysis. Part 12. Mechanism of the Reaction of Optically Active 1-(p-Methoxyphenyl)ethyl Trifluoroacetate with Phenol and Metanol in Benzene and Cyclohexane

DOI: 10.1039/P29800000842

Source and publish data:

Journal of the Chemical Society. Perkin transactions II p. 842 - 848 (1980)

Update date:2022-08-17

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Authors:

Okamoto, KunioOkamoto, Kunio

Takeuchi, Ken'ichiTakeuchi, Ken'ichi

Inoue,TakeshiInoue,Takeshi

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Article abstract of DOI:10.1039/P29800000842

The rate, product distribution, and stereochemical course for the reactions of 0.05-0.1M-1-(p-methoxyphenyl)ethyl trifluoroacetate (1) with methanol and phenol have been investigated in benzene or cyclohexane as solvent at 25.0 deg C.Below 1E-3M-methanol or -phenol the total kinetic order is two overall .The rates are virtually independent of the pyridine used to bind the trifluoroacetic acid produced.The major product from the phenol reaction, 1-(p-methoxyphenyl)ethyl phenyl ether, shows net retention (6-9percent) of configuration along with predominant racemization.In addition, the methyl ether product from the methanol reaction also undergoes net retention (24percent with 0.2M-methanol).The formation of the ethers with net retention of configuration can be accounted for by an intermolecular SNi mechanism.

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