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Syntheses, Structures, and Reactivity of 1‐Phosphanylnaphth‐2‐ols
Author(s) -
Heinicke Joachim,
Kadyrov Renat,
Kindermann Markus K.,
Kloss Matthias,
Fischer Axel,
Jones Peter G.
Publication year - 1996
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19961290914
Subject(s) - chemistry , protonation , reactivity (psychology) , silylation , chelation , lithium (medication) , stereochemistry , bond cleavage , solid state , medicinal chemistry , cleavage (geology) , crystallography , organic chemistry , catalysis , ion , medicine , alternative medicine , geotechnical engineering , pathology , fracture (geology) , engineering , endocrinology
P‐tertiary or amino‐substituted 1‐phosphanylnaphth‐2‐yl silyl ethers 3 are synthesized by stepwise reaction of lithium 1‐lithio‐2‐naphtholate 1 with chlorophosphanes and ClSiMe 3 . The free phosphanylnaphthols 4 are prepared by alcoholysis. As established by characteristic coupling constants and X‐ray structural analyses (of 3c, 4c ), 3 exhibit in solution and in the solid state a cis ‐bisecting conformation, whereas 4 prefers the opposite trans ‐bisecting arrangement, allowing easy protonation and formation of chelate complexes. Substitution reactions of phosphanylnaphtholates 2 with Ph 2 PCl and formation of chelate complexes LNi‐η 5 ‐Cp and L 2 Pd are described. Attempts to prepare secondary and primary phosphanylnaphthols failed because of facile cleavage of the P–C(naphthyl) bond in PH‐substituted 1‐phosphanylnaphth‐2‐ols.