Tetrahedron

Experimental studies of the anomeric effect. part III. Rotameric preferences about the exo-cyclic c 2-x bond in equatorial and axial 2-methoxy-and 2-methylamino- …

H Booth, JM Dixon, KA Khedhair, SA Readshaw

Index: Booth, Harold; Dixon, J. Mark; Khedhair, Khedhair A.; Readshaw, Simon A. Tetrahedron, 1990 , vol. 46, # 5 p. 1625 - 1652

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Citation Number: 24

Abstract

Values of 3 J (CC), 3J (CH), 4J (CH) and 3J (HH), supported by nO enhancements, in nmr spectra of 2-methoxy-and 2-methyl-amino-tetrahydropyrans, point to a very strong preference for rotamers in which an exo-cyclic heteroatom lone pair is antiperiplanar to the endo-cyclic C2-O bond (“exo-anomeric effect”)