Anomeric effect enhancement in C-5-substituted 2-methoxytetrahydropyrans

RM Srivastava, AC Pavão, GM Seabra…

Index: Srivastava; Pavao; Seabra; Brown Journal of Molecular Structure, 1997 , vol. 412, # 1-2 p. 51 - 58

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Abstract

cis-and trans-2, 5-Dimethoxytetrahydropyrans, cis-2, 5-dimethoxy-6-methyltetrahydropyran and 2-methoxy-5-methyltetrahydropyran have been examined to see the effect of an OCH3 group at position 5 on the degree of anomeric effect in substituted 2- methoxytetrahydropyrans. The present study shows that this group stabilises the C-2 electronegative substituent in the axial position. Semi-empirical and ab initio molecular ...

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