Cinchona Alkaloids as Versatile Ambivalent Ligands – Coordination of Transition Metals to the Four Potential Donor Sites of Quinine
✍ Scribed by Roland Hubel; Kurt Polborn; Wolfgang Beck
- Publisher
- John Wiley and Sons
- Year
- 1999
- Tongue
- English
- Weight
- 421 KB
- Volume
- 1999
- Category
- Article
- ISSN
- 1434-1948
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✦ Synopsis
A series of metal complexes in which quinine (L 1 ) and CF 3 SO 3 -(M = Pd, Pt, 20-22) and (L 2 +H + )(ZnCl 3 -) (23). Quinine and cinchonine act as N,O-N bridge in the cinchonine (L 2 ) are coordinated via the four possible donor atoms was prepared and characterized. Coordination of the complexes (R 3 P)(Cl)M(µ-L 1 -H + )M(Cl) 2 (PR 3 ) (M = Pd, Pt, 24, 25, 27, 28), (Cp*)(Cl)Ir(µ-L 1 -H 1 )Ir(Cl) 2 (Cp*) (29), (EtP 3 )-tertiary N atom of quinine is observed in [L 1 MPPh 3 ] + NO 3 -[M = Au (1), Ag (2)], [L 1 Pd(COD)(Cl)] + NO 3 -(3) and (Cl)Pd(µ-L 2 -H + )Pd(Cl) 2 (PEt 3 ) (26), and as N-N bridge in the complexes [(Ph 3 P)Au(µ-L 1 )Au(PPh 3 )] + NO 3 -(30) and (allyl)-L 1 Pd(Cl)(allyl) (4). The mono anion of quinine functions as N,O chelate ligand in (L 1 -H + )M(Cl)(PR 3 ) (M = Pd, Pt, 5-10), (Cl)Pd(µ-L 1 )Pd(Cl)(allyl) (31). Coordination of quinine via the C=C double bond occurs in [(L 1 +2 H + )PtCl 3 ] + Cl -(32). The [(L 1 -H + )Pd(en)] + NO 3 -(11) and (L 1 -H + ) 2 TiCl 2 (12). Protection of the tertiary N atom of quinine by methylation or structures of 11, 13, 19, 23, 26 and 32 were determined by Xray diffraction. In most cases the coordination mode and the protonation allows the synthesis of the quinoline complexes [(L 1 CH 3 + )M(Cl) 2 (PR 3 )] + BF 4 -[ ] Part CXII: Ref. [1]
signed by 2D-COSY experiments) of the hydrogen atoms