The dirhodium-method in the determination of absolute configurations of phospholene chalcogenides.
The 1H, 13C, and 31P NMR signals of six chiral phospholene chalcogenides (X = O, S, Se) are duplicated in the presence of one mole equivalent of the chiral auxiliary Rh2[(R)-MTPA]4 (diastereomeric dispersion Deltanu; in Hz). The samples were investigated as nonracemic mixtures of enantiomers with known absolute configurations so that signs can be attributed to the Deltanu-values and each signal set can be assigned to the respective enantiomer. The signs are uniform--in particular those of 1H nuclei--and nearly independent of the nature of the chalcogen atom. Thus, if the absolute configuration of one compound is known, it is possible to derive absolute configurations in the whole series (correlation method).
Moeller
Stefan
S
Universität Hannover, Institut für Organische Chemie, Hannover, Germany.
Drzazga
Zbigniew
Z
Pakulski
Zbigniew
Z
Pietrusiewicz
K Michał
KM
Duddeck
Helmut
H
D000096:Acetone / Q000737:chemistry; D019256:Cadmium Chloride / Q000737:chemistry; D018011:Chalcogens / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry*; D010756:Phosphoric Acids / Q000737:chemistry; D012015:Reference Standards; D012238:Rhodium / Q000032:analysis / Q000737:chemistry*; D012995:Solubility; D013237:Stereoisomerism
D018011:Chalcogens; D009943:Organophosphorus Compounds; D010756:Phosphoric Acids; C013194:phospholenes; D000096:Acetone; D012238:Rhodium; C030242:phosphoric acid; D019256:Cadmium Chloride