Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Organometallics called Regioselective Electrophilic Substitution and Addition Reactions at an N-Coordinated Pyrrolyl Ligand in (PMe2Ph)3Cl2Re(NC4H4), Author is DuBois, M. Rakowski; Vasquez, Lisa D.; Peslherbe, L.; Noll, B. C., which mentions a compound: 616-43-3, SMILESS is CC1=CNC=C1, Molecular C5H7N, Category: chiral-oxygen-ligands.
The reaction of excess pyrrolyllithium with mer-(PMe2Ph)3ReCl3 gives the air-stable product mer-(PMe2Ph)3Cl2Re(NC4H4) (1), which was characterized by spectroscopic techniques and by an x-ray diffraction study. 1 Reacts with electrophiles to form new Re(III) complexes with regioselectively substituted pyrrolyl ligands. For example, reaction with 1 equiv of N-chlorosuccinimide forms the complex with a 3-chloropyrrolyl ligand, while reaction with excess reagent produces the 3,4-dichloropyrrolyl and 2,3,4-trichloropyrrolyl complexes. The regiochem. of the reactions was established from 1H NMR data, and the structure of the dibrominated (PMe2Ph)3Cl2Re(3,4-NC4H2Br2) (5) was confirmed by x-ray diffraction. Reaction of 1 with Me triflate produces after workup (PMe2Ph)3Cl2Re(3-NC4H3Me) (6), and further reaction of 6 with Me triflate yields (PMe2Ph)3Cl2Re(3,4-NC4H2(Me)2) (7). In contrast, triflic acid protonates the pyrrolyl ligand of 1 at the α-C to form [(PMe2Ph)3Cl2Re(NC4H5)]OTf (8), which was identified by an x-ray diffraction study. The Michael addition of di-Me acetylenedicarboxylate to the β-C of the pyrrolyl ligand in 1 also was characterized. Methods for the removal of the substituted pyrrolyl ligands from the Re center are described.
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Reference:
Synthesis and Crystal Structure of a Chiral C3-Symmetric Oxygen Tripodal Ligand and Its Applications to Asymmetric Catalysis,
Chiral lanthanide(III) complexes of sulphur–nitrogen–oxygen ligand derived from aminothiourea and sodium D-camphor-β-sulfonate