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The synthesis and some NMR properties of 2,3‐bis(diphenylphosphino)‐6‐phenyl‐λ 3 ‐phosphinine
Author(s) -
Holah David G.,
Hughes Alan N.,
Knudsen Karen L.,
Perrier Richard
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250122
Subject(s) - chemistry , acetylene , context (archaeology) , ligand (biochemistry) , crystallography , nuclear magnetic resonance spectroscopy , stereochemistry , organic chemistry , paleontology , biochemistry , receptor , biology
The synthesis, from 1,2,5‐triphenylphosphole and bis(diphenylphosphino)acetylene, of 2,3‐bis(diphenylphosphino)‐6‐phenyl‐λ 3 ‐phosphinine, the first example of a λ 3 ‐phosphinine bearing phosphorus‐containing side chains, is reported. This compound shows in its nmr spectrum the largest value of 3 J pp (178 Hz) yet reported for a system containing the P III ‐C‐C‐P III linkage. Evidence is presented which supports the idea that this extraordinarily large coupling arises as a result of geometrical factors which place the non‐bonding electron pairs of the two side‐chain P atoms in very close proximity to one another. Reactions of the λ 3 ‐phos‐phinine with Ni(II) and Pt(II) compounds are briefly discussed in the context of the nmr properties of both the ligand and the complexes formed.