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 ...
[Hartung, Jens; Kneuer, Rainer; Rummey, Christian; Bringmann, Gerhard Journal of the American Chemical Society, 2004 , vol. 126, # 38 p. 12121 - 12129]
