Synthesis and Structure of σ-Complexes of the Chiral Rhenium Lewis Acid [(η5-C5H5)Re(NO)(PPh3)]+ and Aromatic Nitrogen Heterocycles
Open Access
- 1 August 1992
- journal article
- Published by Walter de Gruyter GmbH in Zeitschrift für Naturforschung B
- Vol. 47 (8) , 1175-1184
- https://doi.org/10.1515/znb-1992-0820
Abstract
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)(PPh3)(CN). The crystal structures of 3 (triclinic, P1̄, a = 9.879(1) A, b = 16.677(2) A, c = 9.962(1) Å, α = 91.477(3)°, β = 99.155(3)°, γ = 100.633(3)°, Ζ = 2) and 4 (triclinic, P1̄, a = 10.961(2) Å, b = 15.770(2) Å, c = 10.159(1) A, a = 87.65(2)°, β = 109.88(2)°, γ = 101.27(2)°, Z = 2) are determined, and the Re—N conformations analyzed.Keywords
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