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• W2000714102 abstract "Carbon-13 and 31P NMR data are reported for 1-phenyl-4-phosphorinanone and its 1-selenide, as well as for two anancomeric 1-phenyl-3,5-dimethyl-4-phosphorinanones and their 1-selenides. The conformational free energy of the P-phenyl substituent in 1-phenyl-4-phosphorinanone is estimated to be ΔG° = 0.81 kcal mol−1 (ca 80% axial) in chloroform, and this result is consistent with both 13C NMR shielding and coupling data. The γ effects of a single atom substituent on phosphorus are found to be small in the case of selenium; information in the literature indicates significant downfield-shifting γe effects due to equatorial oxygen and sulphur substituents in phosphorinanes. In selenides, the shift for the aromatic C-ipso carbon in the axial isomer is further downfield than in the equatorial isomer, an observation not precedented in the literature. In the discussion of P-C coupling data a ‘second order’ Karplus-like relationship is invoked for 3J(PC), which is dependent both on the dihedral angle and on the orientation of the phosphorus lone pair in phosphines. The one-bond P-C-ipso coupling in selenides is identical for all three selenides studied, regardless of the stereochemistry at phosphorus. Similar lack of substantial differentiation is noted for one-bond P-Se coupling. A possible origin of this phenomenon is discussed in terms of diminution of the phosphorus charge contribution to the Fermi contact term. From 31P NMR data a high stereodependence of selenylation shifts is apparent, and greater shifts (by ca 20 ppm) are observed when selenium is bound to phosphorus in the more crowded (axial) position. In anancomeric (conformationally biased) phosphines, the isomer with the axial phenyl group has the 31P signal at lower field. This is consistent with observations made previously for rigid 1-phenylphosphorinanes." @default.
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• W2000714102 date "1983-06-01" @default.
• W2000714102 modified "2023-09-23" @default.
• W2000714102 title "13C and31P NMR studies of configurational and conformational effects in 1-Phenyl-4-phosphorinanones and their 1-selenides" @default.
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• W2000714102 doi "https://doi.org/10.1002/omr.1270210602" @default.
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