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Assignment of relative configuration in cyclopentenes from proton chemical shift increments
Author(s) -
Hunter G.,
Miller J. A.,
Moore M.,
Ullah G. M.
Publication year - 1983
Publication title -
organic magnetic resonance
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.483
H-Index - 72
eISSN - 1097-458X
pISSN - 0030-4921
DOI - 10.1002/omr.1270210411
Subject(s) - vicinal , proton , shielding effect , electromagnetic shielding , chlorine , chemistry , chlorine atom , coupling (piping) , stereochemistry , computational chemistry , medicinal chemistry , physics , materials science , organic chemistry , nuclear physics , quantum mechanics , metallurgy
The ‘ syn ‐upfield’ rule for vicinal shielding by methyl and chlorine substituents has been confirmed for a series of 4‐chlorocyclopentenes, and used to make configurational assignments in cases where conclusions based on vicinal proton coupling are not reliable. The methoxymethyl group should be added to those substituents whose effect on vicinal protons can be deshielding, irrespective of geometry.