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17 O NMR study of isomeric 2‐R‐2‐oxo‐1,3,2‐dioxaphosphorinanes
Author(s) -
Bock Paul L.,
Mosbo John A.,
Redmon John L.
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.1270210808
Subject(s) - chemistry , oxygen , chemical shift , stereochemistry , phosphorus 31 nmr spectroscopy , nmr spectra database , oxygen atom , nuclear magnetic resonance spectroscopy , spectral line , crystallography , medicinal chemistry , molecule , organic chemistry , physics , astronomy
Oxygen‐17 NMR spectra were obtained from the four pairs of isomeric 2‐R‐2‐oxo‐1,3,2‐dioxaphosphorinanes, where R=OMe (2), NMe 2 (3), H (4) or Me (5). The isomerism has been previously shown to be configurational at phosphorus, with one isomer of each pair having an equatorial phosphoryl oxygen (a isomer), and the other an axial orientation for phosphoryl oxygen (b isomer). Only data for the phosphoryl oxygen are reported. Substitution of OMe or NMe 2 for H or Me produced upfield shifts of 27.9‐41.8 ppm. In all cases, the chemical shifts of the a isomers were upfield of the b analogs, with differences of 7.9, 18.0, 20.3 and 8.6 ppm for 2—5, respectively. The absolute values of 1 J ( 31 P 17 O) were 5–9 Hz larger for the a isomers.