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Issue 1, 2016
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Zwitterionic and biradicaloid heteroatomic cyclopentane derivatives containing different group 15 elements

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Abstract

The formal cyclopentane-1,3-diyl derivatives [E1(μ-NTer)2({E2C} = NDmp)] (Ter = 2,6-dimesityl-phenyl, Dmp = 2,6-dimethylphenyl) were prepared by 1,1-insertion of CNDmp into the N–E2 bond of [E1(μ-NTer)2E2] (E1 = N, P; E2 = P, As). The insertion does not occur for E1 = E2 = As or E2 = Sb. Dependent on the choice of formal radical centres E, either a biradicaloid or a zwitterion was obtained. The biradicaloid features a P and an As radical center and its biradical character was established by computations as well as characteristic reactivity with respect to the formation of a housane derivative and the activation of molecules bearing multiple bonds, which was demonstrated using the example of PCtBu. In contrast, the formally N,As- and N,P-centered biradicaloids are better regarded as zwitterionic species in accord with computations and diminished reactivity, as neither housane formation nor activation of multiple bonds could be observed.

Graphical abstract: Zwitterionic and biradicaloid heteroatomic cyclopentane derivatives containing different group 15 elements

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Publication details

The article was received on 17 Sep 2015, accepted on 26 Oct 2015 and first published on 27 Oct 2015


Article type: Edge Article
DOI: 10.1039/C5SC03515E
Citation: Chem. Sci., 2016,7, 745-751
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    Zwitterionic and biradicaloid heteroatomic cyclopentane derivatives containing different group 15 elements

    A. Hinz, A. Schulz and A. Villinger, Chem. Sci., 2016, 7, 745
    DOI: 10.1039/C5SC03515E

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