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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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Article information


Submitted
17 Sep 2015
Accepted
26 Oct 2015
First published
27 Oct 2015

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2016,7, 745-751
Article type
Edge Article
Author version available

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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