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Bis(diethylamino)pentafluorophenylphosphane as Valuable Precursor for the Design of Tetrafluorophenylphosphanes, Tetrafluorophenylphosphinic and ‐phosphonic Acids
Author(s) -
Alter Christian,
Neumann Beate,
Stammler HansGeorg,
Hoge Berthold
Publication year - 2018
Publication title -
european journal of inorganic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 1434-1948
DOI - 10.1002/ejic.201701402
Subject(s) - chemistry , hydrolysis , lithium (medication) , medicinal chemistry , fluorine , nitrogen atom , catalysis , stereochemistry , organic chemistry , group (periodic table) , medicine , endocrinology
Facile replacement of the p ‐fluorine atom in bis(diethylamino)pentafluorophenylphosphane [(Et 2 N) 2 PC 6 F 5 ] by organolithium derivatives LiR (R = CH 3 , n ‐Bu, Ph), lithium alkoxides (R = OMe, OEt) and amides (NMe 2 , NEt 2 ) is described. The obtained phosphanes p ‐R‐C 6 F 4 ‐P(NEt 2 ) 2 are fully characterized. Their acid‐catalyzed hydrolysis affords the corresponding phosphinic acids p ‐R‐C 6 F 4 ‐P(O)(H)OH, which are smoothly oxidized by treatment with a mixture of DMSO/I 2 to phosphonic acids p ‐R‐C 6 F 4 ‐P(O)(OH) 2 .