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Synthesis, properties and complexation of (pS)-1-isocyano-2-methylferrocene, the first planar-chiral isocyanide ligand
Authors:David M. McGinnis
Affiliation:Department of Chemistry, The University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045, United States
Abstract:Reaction of enantiomerically pure, planar-chiral (pS)-1-bromo-2-methylferrocene (1) with phthalimide in the presence of Cu2O produces (pS)-1-phthalimido-2-methylferrocene (2), quantitative reduction of which with hydrazine hydrate affords (pS)-1-amino-2-methylferrocene (3) with >99% ee. Formylation of amine 3 followed by dehydration of the resulting (pS)-1-formamido-2-methylferrocene (4) provides (pS)-1-isocyano-2-methylferrocene (5), the first example of a planar-chiral isocyanide ligand, in a good yield. Isocyanide 5 reacts with PdI2 to give the crystallographically characterized chiral complex trans-[PdI2{(pS)-1-isocyano-2-methylferrocene}2] (6). The redox behavior of 4, 5, and 6, accessed by cyclic voltammetry, is discussed.
Keywords:Isocyanide ligands   Planar chirality   Palladium(II) complex
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