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- W2114314538 abstract "The 13 C nuclear magnetic resonance data of a series of 2-(4-substituted-phenoxy)tetrahydropyrans at 156 K and in CF 2 Br 2 and CHFCl 2 solvents show that the axial preference increases with electron withdrawal in the aryloxy group: from 79% (ΔG° E→A = −0.4 kcal mol −1 ) (4-OCH 3 ) to 90% (ΔG° E→A = −0.7 kcal mol −1 ) (4-NO 2 ) in CF 2 Br 2 . The axial preference (anomeric effect) is smaller in the more polar CHFCl 2 solvent, as expected, and the substituent effect is smaller also: change in ΔG° E→A from −0.3 (4-OCH 3 ) to −0.5 (4-NO 2 ) kcal mol −1 . However, the axial preference of 2-acetoxytetrahydropyran is shown to be smaller than that of 2-phenoxytetrahydropyran in CF 2 Br 2 solvent although the acetoxy group is expected to be more electronegative than the phenoxy group. Furthermore, the polarity of the solvent has no effect on the conformational equilibrium of 2-acetoxytetrahydropyran. The results are interpreted in terms of both orbital and electrostatic interactions. The ring-inversion barrier of 2-alkoxy and 2-aryloxytetrahydropyrans, determined by the temperature-coalescence method, is lower than that of tetrahydropyran by about 1.5 kcal mol −1 . Key words: 2-substituted tetrahydropyrans, conformational analysis, anomeric effect, ring inversion." @default.
- W2114314538 created "2016-06-24" @default.
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- W2114314538 date "1991-03-01" @default.
- W2114314538 modified "2023-09-23" @default.
- W2114314538 title "The conformational behaviour of 2-aryloxytetrahydropyrans and 2-acetoxytetrahydropyran, and barrier to ring inversion" @default.
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- W2114314538 doi "https://doi.org/10.1139/v91-071" @default.
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