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Issue 5, 2017
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(Phosphanyl)phosphaketenes as building blocks for novel phosphorus heterocycles

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Abstract

Although BH3 simply coordinates the endocyclic P of (phospholidino)phosphaketene 1Dipp, the bulkier B(C6F5)3 gives rise to a zwitterionic diphosphirenium, which is a novel type of 2π-electron aromatic system as shown by the calculated NICS values. While the reaction of 1Dipp with Na[PCO(dioxane)x] is unselective, the same reaction with the sterically bulky (phospholidino)phosphaketene 1Ar** [Ar** = 2,6-bis[di(4-tert-butylphenyl)methyl]-4-methylphenyl selectively affords a sodium bridged dimer containing a hitherto unknown λ353-triphosphete core. The latter formally results from “P” addition to a 1,3-P/C-dipole. Similarly, adamantyl isonitrile adds to 1Dipp giving a 4-membered phosphacycle. In contrast to 1, the phosphaketene derived from the electrophilic diazaphospholidine-4,5-dione is unstable and reacts with a second molecule of Na[PCO(dioxane)x] to afford a 1,3,4-oxadiphospholonide derivative.

Graphical abstract: (Phosphanyl)phosphaketenes as building blocks for novel phosphorus heterocycles

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Publication details

The article was received on 20 Jan 2017, accepted on 07 Mar 2017 and first published on 08 Mar 2017


Article type: Edge Article
DOI: 10.1039/C7SC00300E
Citation: Chem. Sci., 2017,8, 3720-3725
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    (Phosphanyl)phosphaketenes as building blocks for novel phosphorus heterocycles

    M. M. Hansmann, D. A. Ruiz, L. (. Liu, R. Jazzar and G. Bertrand, Chem. Sci., 2017, 8, 3720
    DOI: 10.1039/C7SC00300E

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