EXPERIMENTAL STUDIES OF THE ANOMERIC EFFECT .3. ROTAMERIC PREFERENCES ABOUT THE EXOCYCLIC C2-X BOND IN EQUATORIAL AND AXIAL 2-METHOXYHYDROPYRANS AND 2-METHYLAMINO-TETRAHYDROPYRANS

被引:29
作者
BOOTH, H
DIXON, JM
KHEDHAIR, KA
READSHAW, SA
机构
[1] Department of Chemistry, University of Nottingham, Nottingham
关键词
D O I
10.1016/S0040-4020(01)81971-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Values of 3 J(CC), 3J(CH), 4J(CH) and 3J(HH), supported by n.O.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"). © 1990.
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页码:1625 / 1652
页数:28
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