Dibenzo[<i>b,d</i>]phosphorin

Koe, P. de; Veen, R. Van; Bickelhaupt, F. Matthias

doi:10.1002/anie.196804653

“…Seven steps were needed to synthesize the unstable parent species which was only characterised by UV spectroscopy and mass spectrometry. 1 Later, through another route, the P-W(CO) 5 complex was detected by 31 P NMR spectroscopy and some reactions of its PvC double bond were described. 2 Apart from this, the stable 6-phenyl derivative was obtained by two groups, 3,4 but its chemistry was not reported.…”

mentioning

confidence: 99%

6-Methoxy-5-phosphaphenanthrene: a molecule with an unreactive PC double bond

Wang

¹

,

Wang

²

,

Wang

³

et al. 2015

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A multi-step synthesis of the title compound has been devised. In spite of its P=C double bond, the compound does not react at 100 °C with methanol and 2,3-dimethyl-1,3-butadiene. DFT calculations indicate a planar core, a long P=C double bond at 1.725 Å and a high-lying LUMO. Complexation can force the methoxy substituent to rotate out of the plane, thus restoring partly the double bond character of the P=C bond.

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“…[8] On reaction with a cyclic phosphinic acid, the same (C 6 H 5 ) 2 SiH 2 gave a 92% yield of secondary cyclic phosphane. [9] In the present work, both the silanes and LiAlH 4 were used, depending on the starting phosphinic acid. With the monophosphinic acids 1؊3, PhSiH 3 was found to be convenient.…”

Section: Reduction Of Phosphinic Acids 1؊6 To Secondary Phosphanesmentioning

confidence: 99%

Phosphane and Bis(phosphane) Ligands from Phosphinic Acids

Soulier

¹

,

Yaouanc

²

,

Laurent

³

et al. 2000

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The Boyd−Regan methodology allowed for access to various cyclic or benzylic mono‐ and bis(phosphinic acids) 1−6. The reduction of monophosphinic acids to secondary phosphanes 7−9 was achieved with silanes. On the other hand, reduction of the bis(phosphinic acids) with LiAlH4 led to bis(phosphanes) 12−13. Various cyclic phosphanes and bis(phosphanes) were obtained by the alkylation of these secondary phosphanes (as their borane adducts). The Michael addition of the same borane adducts to vinylic phosphonates led to phosphane−phosphonates which could be hydrolysed to new hydrosoluble phosphanes.

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“…[8] On reaction with a cyclic phosphinic acid, the same (C 6 H 5 ) 2 SiH 2 gave a 92% yield of secondary cyclic phosphane. [9] In the present work, both the silanes and LiAlH 4 were used, depending on the starting phosphinic acid. With the monophosphinic acids 1؊3, PhSiH 3 was found to be convenient.…”

Section: Reduction Of Phosphinic Acids 1؊6 To Secondary Phosphanesmentioning

confidence: 99%