N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid

Rottschäfer D, Neumann B, Stammler H-G, Ghadwal R (2017)
CHEMISTRY-A EUROPEAN JOURNAL 23(38): 9044-9047.

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Abstract
Four-membered biradicaloid compounds containing a N2E2 (E = main group element) framework have been thoroughly investigated; however, the synthesis of stable analogues with a C2P2 skeleton remains a challenge. Base-mediated double C-H functionalization of IPr = CH2 (1) (IPr = C[N(2,6-iPr(2)-C6H3) CH](2)) with PCl3 affords [{(IPr) CP}(2)Cl]Cl (2) as a royal blue solid. Treatment of 2 with KC8 yields the stable phosphorus biradicaloid [(IPr) CP](2) (3) featuring a four-membered C2P2 ring. Compound 3 is diamagnetic and shows sharp and temperature-independent NMR resonances, revealing its singlet biradicaloid nature. The stability of 3 is attributed to the sigma- and pi-electron-donating property of the N-heterocyclic vinylidene [(IPr) C] group.
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Rottschäfer D, Neumann B, Stammler H-G, Ghadwal R. N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL. 2017;23(38):9044-9047.
Rottschäfer, D., Neumann, B., Stammler, H. - G., & Ghadwal, R. (2017). N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL, 23(38), 9044-9047. doi:10.1002/chem.201702433
Rottschäfer, D., Neumann, B., Stammler, H. - G., and Ghadwal, R. (2017). N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL 23, 9044-9047.
Rottschäfer, D., et al., 2017. N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL, 23(38), p 9044-9047.
D. Rottschäfer, et al., “N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid”, CHEMISTRY-A EUROPEAN JOURNAL, vol. 23, 2017, pp. 9044-9047.
Rottschäfer, D., Neumann, B., Stammler, H.-G., Ghadwal, R.: N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid. CHEMISTRY-A EUROPEAN JOURNAL. 23, 9044-9047 (2017).
Rottschäfer, Dennis, Neumann, Beate, Stammler, Hans-Georg, and Ghadwal, Rajendra. “N-Heterocyclic Vinylidene-Stabilized Phosphorus Biradicaloid”. CHEMISTRY-A EUROPEAN JOURNAL 23.38 (2017): 9044-9047.
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