Conformational analysis. 42. Monosubstituted tetrahydropyrans
EL Eliel, KD Hargrave, KM Pietrusiewicz…
Index: Eliel,E.L.; Hargrave,K.; Pietrusiewisz,K. Journal of the American Chemical Society, 1982 , vol. 104, p. 3635
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Citation Number: 103
Abstract
Abstract: The conformational energies of 2-, 3-, and 4-methyl, 2-vinyl, 2-ethinyl, 2-ethyl, 2- carbomethoxy, and 2-hydroxymethyl substituents in tetrahydropyran have been determined (in kcal/mol): 2-Me, 2.86; 3-Me, 1.43; 4-Me, 1.95; 2-CH2= CH, 2.27; 2-CHsC, 0.34; 2-Et, 2.62; 2-C02Me, 1.38; 2-CH20H, 2.89. Some of these values differ appreciably from earlier reported ones, and the 2-C02Me value does not support the hypothesis of a reverse ...
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