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Issue 47, 2018
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Imino-stabilised phosphinidene (or azaphosphole?) and some of its derivatives

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Abstract

Diiminophenyl (dimph) proved to be an excellent ligand platform to stabilise a low-valent phosphorus centre. The resultant compound dimphP (3), which can be rationalized as an imino-stabilised phosphinidene or benzoazaphosphole, shows remarkable chemical stability: it withstands treatment with water and oxidizers (O2 and pyridine oxide) and only reacts with excess strong acid (e.g. HCl) to generate the P(III) chloride (dimHph)PCl (7), where dimHph stands for a diiminophenyl group hydrogenated at one imine position. Surprisingly, substitution of the chloride under some nucleophilic (KOBut) and electrophilic conditions (Me3SiOTf) regenerates the parent compound 3, by proton removal from the weakly acidic CH2N position. A related species (dimH2ph)P (14), where dimH2ph stands for diiminophenyl hydrogenated to imino(aminomethyl)phenyl, is produced upon thermal rearrangement of the hydride (dimHph)PH (13). X-ray structures of compounds 3, 14, and (dimHph)PO2CH (17) are also discussed.

Graphical abstract: Imino-stabilised phosphinidene (or azaphosphole?) and some of its derivatives

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Publication details

The article was received on 24 Aug 2018, accepted on 12 Nov 2018 and first published on 12 Nov 2018


Article type: Paper
DOI: 10.1039/C8DT03465F
Citation: Dalton Trans., 2018,47, 17011-17019
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    Imino-stabilised phosphinidene (or azaphosphole?) and some of its derivatives

    M. T. Nguyen, B. Gabidullin and G. I. Nikonov, Dalton Trans., 2018, 47, 17011
    DOI: 10.1039/C8DT03465F

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