Dynamic Covalent Chemistry Approach toward 18-Membered P4N2 Macrocycles and Their Nickel(II) Complexes
| Autor: | Elvira I. Musina, Evamarie Hey-Hawkins, Peter Lönnecke, L. I. Musin, Igor A. Litvinov, Andrey A. Karasik, Anna S. Balueva, Oleg G. Sinyashin, Alena S. Shpagina, Tatiana I. Wittmann |
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| Rok vydání: | 2020 |
| Předmět: |
010405 organic chemistry
Chemistry Ligand Organic Chemistry Dynamic covalent chemistry chemistry.chemical_element Butane Nuclear magnetic resonance spectroscopy 010402 general chemistry Condensation reaction 01 natural sciences 0104 chemical sciences Nickel Crystallography chemistry.chemical_compound Stereoselectivity Lone pair |
| Zdroj: | The Journal of Organic Chemistry. 85:14610-14618 |
| ISSN: | 1520-6904 0022-3263 |
| DOI: | 10.1021/acs.joc.0c01317 |
| Popis: | A dynamic covalent chemistry approach was used for the stereoselective synthesis of 1,10-diaza-3,8,12,17-tetraphosphacyclooctadecanes via condensation reaction of 1,4-bis(organylphosphino)butane, formaldehyde, and primary amines. The obtained 18-membered P4N2 macrocycles were isolated in pure form as meso- (RPSPSPRP) or rac- (RPRPRPRP/SPSPSPSP) isomers. The structural features of the individual stereoisomers were revealed by NMR spectroscopy and X-ray structure analysis. All P4N2 macrocycles form square-planar nickel(II) complexes with the RPSPSPRP isomer only, in which the orientation of the lone pairs of electrons at phosphorus favors this coordination mode, independent of the initial configuration of the ligand, indicating the ability of the 18-membered P4N2 macrocycles to stereoisomerize in the course of the complexation. |
| Databáze: | OpenAIRE |
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