Conformational analysis. XXXI. Conformational equilibria of 1, 3-dioxanes with polar substituents at C-5

MK Kaloustian, N Dennis, S Mager…

Index: Kaloustian,M.K. et al. Journal of the American Chemical Society, 1976 , vol. 98, p. 956 - 965

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Citation Number: 70

Abstract

Abstract: The positions of equilibrium, established by acid catalysis, between epimeric 2- isopropyl-5-Xl, 3-dioxanes in which X is CH20CH3, OCOCH3, COCH3, COOCH,, COO-, SCH3, S (CH&+, SOCH3, S02CH3, NO2, NH3+, NH (CH3) 2+, N (CH3) 3+ are reported and compared with previously published data for X= Me, 2 F, CI, Br, CN, 3 CH30, CzH50, 4 CHIOH, and OH.'In a number of these cases the axial (cis) isomers are favored at ...