Study of the anomeric effect in 2-substituted 1,3-dithianes |
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| Affiliation: | 1. A.E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Scientific Center, Russian Academy of Sciences, Kazan 420088, Russian Federation;2. Max Planck Institute for Dynamics of Complex Technical Systems, Magdeburg D-39106, Germany |
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| Abstract: | The conformational analysis of several 2-substituted 1,3-dithianes made possible the evaluation of S-C-Y anomeric interactions, where Y = SCH3, SC6H5, CO2CH3, CO6H5, CO2H and N(CH3)2. The relative magnitude of the effects observed for these groups [ΔG°dithiane(Y) - ΔGδ cyclohexane(Y)] can be explained in terms of the combined influence of dipole/dipole and two-electron stabilizing interactions (stereoelectronic effect). |
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