Short Note
Version 1
Preserved in Portico This version is not peer-reviewed
N-(diisopropylphosphanyl)benzamide
Version 1
: Received: 31 May 2023 / Approved: 31 May 2023 / Online: 31 May 2023 (13:21:49 CEST)
A peer-reviewed article of this Preprint also exists.
Alcaide, M.M.; Garrido, D.G.; Álvarez, E.; Peloso, R. N-(diisopropylphosphanyl)benzamide. Molbank 2023, 2023, M1667. Alcaide, M.M.; Garrido, D.G.; Álvarez, E.; Peloso, R. N-(diisopropylphosphanyl)benzamide. Molbank 2023, 2023, M1667.
Abstract
N-(diisopropylphosphanyl)benzamide, PhC(O)NHPiPr2, has been synthesized in good yield following two alternative procedures that employ benzamide as the starting material. The first one is a two-step preparation, in which N-(trimetilsilyl)benzamide is reacted with PiPr2Cl, to give the title compound in good yield, whereas the second one is a straightforward synthesis which converts benzamide into N-(diisopropylphosphanyl)benzamide by reaction with PiPr2Cl in the presence of N,N-dimethylpyridin-4-amine (DMAP) and triethylamine. NMR spectroscopy and X-ray diffraction analyses have been performed to characterize the new compound and elucidate its molecular structure in the solid state. N-(diisopropylphosphanyl)benzamide adds to the limited family of amido-substituted phosphines, RC(O)NHPR’2, which can be classified as bidentate hybrid P,O-ligands, both in their neutral and anionic forms, the latter achievable by deprotonation of the NH group.
Keywords
P ligands; P(III) compounds; sterically demanding ligands; hemilabile ligands
Subject
Chemistry and Materials Science, Other
Copyright: This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
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