Synthesis and Structure of σ-Complexes of the Chiral Rhenium Lewis Acid [(η5-C5H5)Re(NO)(PPh3)]+ and Aromatic Nitrogen Heterocycles

@article{Dewey1992SynthesisAS,
  title={Synthesis and Structure of $\sigma$-Complexes of the Chiral Rhenium Lewis Acid [($\eta$5-C5H5)Re(NO)(PPh3)]+ and Aromatic Nitrogen Heterocycles},
  author={Michael A. Dewey and Douglas A. Knight and Atta M. Arif and John A. Gladysz},
  journal={Zeitschrift f{\"u}r Naturforschung B},
  year={1992},
  volume={47},
  pages={1175 - 1184}
}
Reactions of (η5-C5H5)Re(NO)(PPh3)(OTf) (1) with pyridine, quinoline, and isoquinoline give the respective σ-adducts [(η5-C5H5)Re(NO)(PPh3)(NCxHy)]+TfO- (2-4) in 86-95% yields. However, 1 and 8-methylquinoline do not react in refluxing xylene (16 h). Reactions of (+)-(R)-1 with quinoline and isoquinoline give (–)-(S)-3 and (+)-(S)-4. Both products form with retention of configuration at rhenium and in >98% ee, as assayed by subsequent reactions with (CH3CH2)4N+CN- to give (+)-(S)-(η5-C5H5)Re(NO… 
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