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Enantiopure Phospha[1]ferrocenophanes: Textbook Examples of Through‐Space Nuclear Spin–Spin Coupling
Author(s) -
Sadeh Saeid,
Cao My P. T.,
Quail J. Wilson,
Zhu Jianfeng,
Müller Jens
Publication year - 2018
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201801139
Subject(s) - enantiopure drug , chemistry , moiety , metathesis , isopropyl , chirality (physics) , crystallography , coupling (piping) , ferrocene , stereochemistry , medicinal chemistry , organic chemistry , materials science , chiral symmetry , enantioselective synthesis , physics , quantum mechanics , catalysis , polymerization , electrode , electrochemistry , polymer , nambu–jona lasinio model , quark , metallurgy
Three enantiopure phospha[1]ferrocenophanes ( 2 R ) equipped with either a phenyl, an isopropyl, or a tert ‐butyl group at the bridging phosphorus atom were synthesized by a salt‐metathesis approach in isolated yields between 52 and 63 %. The chirality in these strained sandwich compounds stems from the planar‐chiral ferrocene moiety, which is symmetrically equipped with two i Pr groups adjacent to phosphorus. Surprisingly, all three phospha[1]ferrocenophanes show an uncommon through‐space nuclear 1 H– 31 P coupling. As a result of the embedded symmetry, these new compounds are ideal examples to differentiate between through‐space and through‐bond coupling mechanisms in NMR spectroscopy.