The reactions of (-)-(S)-2, MePhPCH2Ph, and (+)-(S)-3, zi-PrMePCH2Ph, with EtO• were shown to yield substitution products MePhPOEt and n-PrMePOEt, respectively. Both reactions occur with net inversion of configuration at phosphorus. The maximum optical yields, determined at very low phosphine conversions, were 96 ± 5% for (-)-(S)-2 and 78 ± 4% for (+)-(S)-3. Optical yields are very sensitive to reaction times and conversions, because the product phosphonites are readily racemized by EtOH formed during reaction. If indeed these substitutions take place via phosphoranyl radicals, then the stereochemistry for reaction of (-)-(S)-2 is consistent with the * electronic configuration and presumed tetrahedral geometry
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1993 magnetic resonance, nuclear quadrupole resonance magnetic resonance, nuclear quadrupole resonance (organic substances) K 2560
-039Inductive Effect, Negative Hyperconjugation, and Gegenion do not Cause the Unusual Properties of the Bicyclo(3.2.1)octa-3,6-dien-2-yl Anion. An NMR Study with Phenyl-Substituted Models.--(CHRISTL, M.; MUELLER, H.; Chem.
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