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- W2024247718 abstract "The solvolysis of 2-phenylethyl-1-C 14 p-toluenesulphonate in absolute ethanol, glacial acetic acid, 90% formic acid, and anhydrous formic acid gave rise to products which showed rearrangements of the C 14 -labeled atoms from the C-1 to the C-2 positions to the extent of 0.3%, 5.5%, 40%, and 45%, respectively. The results constitute an unequivocal proof that phenyl participation occurs in the reactions studied. The different degrees of rearrangement found for the different solvent systems are in agreement with the concept that the solvolysis process may have a range of mechanisms between the two extremes of the nucleophilic or S N 2 type and the limiting or S N 1 type. In the solvolysis in absolute ethanol, a small amount of unreacted 2-phenylethyl p-toluenesulphonate recovered from the reaction mixture was found to show isotope position rearrangement of almost the same degree as the ethanolysis product. This finding is tentatively attributed to the phenomenon of internal return involving an ethyl-phenonium p-toluenesulphonate ion-pair." @default.
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- W2024247718 date "1957-12-01" @default.
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- W2024247718 title "REARRANGEMENT STUDIES WITH C14: V. THE SOLVOLYSIS OF 2-PHENYLETHYL-1-C14p-TOLUENESULPHONATE" @default.
- W2024247718 doi "https://doi.org/10.1139/v57-187" @default.
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