Methanol Addition to Dihapto-Coordinated Rhenium Complexes of Furan
- 24 August 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 123 (37) , 8967-8973
- https://doi.org/10.1021/ja010513l
Abstract
The complexes [TpRe(CO)(L)(4,5-η2-furan)], present as diastereomeric mixtures (L = tBuNC (1A, 1B), PMe3 (2A, 2B), pyridine (3A, 3B), or 1-methylimidazole (4A, 4B)), undergo acid-catalyzed methanol addition in CH2Cl2 at −40 °C, resulting in the syntheses of dihapto-coordinated 2-methoxy-2,3-dihydrofuran complexes. In all cases, two diastereomers resulted, one in which the oxygen of the dihydrofuran is oriented toward the L ligand (5A, 6A, 7A, and 8A), and one in which the oxygen is oriented away from the L ligand (5B, 6B, 7B, and 8B). In all cases, the methoxy group adds stereoselectively, anti to the metal fragment. In addition, the tBuNC complex 1 yields a dihapto-coordinated vinyl ether (5C) that results from ring opening of the protonated furan ligand. In no case does the diastereomeric ratio of products correlate with that of the starting material.Keywords
This publication has 16 references indexed in Scilit:
- Dihapto Coordination of Aromatic Molecules by the Asymmetric π-Bases {TpRe(CO)(L)} (Tp = hydridotris(pyrazolyl)borate; L = tBuNC, PMe3, pyridine, 1-methylimidazole, or NH3)Organometallics, 2001
- Stereoselective Dihapto-Binding of Prochiral Aromatic Compounds by {TpRe(CO)(PMe3)}: Synthesis, Characterization, Stability, and Enantiofacial Discrimination (Tp = Hydrido(tris)pyrazolylborate)Organometallics, 2000
- Dearomatization of Furan: Elementary Transformations of η2-Coordinated Furan Complexes of Pentaammineosmium(II)Journal of the American Chemical Society, 1998
- Safe and Convenient Procedure for Solvent PurificationOrganometallics, 1996
- Face Selection in Reactions of 5,7-Diazaadamantan-2-one Derivatives: Mutual Influence of Remote SubstituentsThe Journal of Organic Chemistry, 1995
- Protonation of an .eta.6-Arene-Metal Complex To Yield a Metal-Hydrogen Bond via an Electrophilic Aromatic Substitution MechanismJournal of the American Chemical Society, 1995
- Dearomatization of Furan: Structure of an .eta.2-Furan Complex and a Survey of Its ReactivityJournal of the American Chemical Society, 1994
- .beta.-Hydride elimination for an amine ligand and the microscopic reverse: the first report of a cis-iminium hydride in equilibrium with its amine precursorJournal of the American Chemical Society, 1992
- Multiple metal-carbon bonds. 32. Rhenium(VII) neopentylidene and neopentylidyne complexes and the x-ray structure of Re(CCMe3)(CHCMe3)(C5H5N)2Organometallics, 1983
- The line-shape analysis of nuclear magnetic resonance peaks broadened by the presence of a 'hidden' exchange partnerCanadian Journal of Chemistry, 1978