Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes

Rottschäfer D, Neumann B, Stammler H-G, van Gastel M, Andrada DM, Ghadwal R (2018)
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57(17): 4765-4768.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
Abstract / Bemerkung
One-electron reduction of C2-arylated 1,3-imidazoli(ni)um salts (IPrAr)Br (Ar=Ph, 3a; 4-DMP, 3b; 4-DMP=4-Me2NC6H4) and (SIPrAr)I (Ar=Ph, 4a; 4-Tol, 4b) derived from classical NHCs (IPr=:C{N(2,6-iPr(2)C(6)H(3))}(2)CHCH, 1; SIPr=:C{N(2,6-iPr(2)C(6)H(3))}(2)CH2CH2, 2) gave radicals [(IPrAr)](center dot) (Ar=Ph, 5a; 4-DMP, 5b) and [(SIPrAr)](center dot) (Ar=Ph, 6a; 4-Tol, 6b). Each of 5a,b and 6a,b exhibited a doublet EPR signal, a characteristic of monoradical species. The first solid-state characterization of NHC-derived carbon-centered radicals 6a,b by single-crystal X-ray diffraction is reported. DFT calculations indicate that the unpaired electron is mainly located at the original carbene carbon atom and stabilized by partial delocalization over the adjacent aryl group.
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ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
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Rottschäfer D, Neumann B, Stammler H-G, van Gastel M, Andrada DM, Ghadwal R. Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 2018;57(17):4765-4768.
Rottschäfer, D., Neumann, B., Stammler, H. - G., van Gastel, M., Andrada, D. M., & Ghadwal, R. (2018). Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 57(17), 4765-4768. doi:10.1002/anie.201801596
Rottschäfer, D., Neumann, B., Stammler, H. - G., van Gastel, M., Andrada, D. M., and Ghadwal, R. (2018). Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57, 4765-4768.
Rottschäfer, D., et al., 2018. Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 57(17), p 4765-4768.
D. Rottschäfer, et al., “Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes”, ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, vol. 57, 2018, pp. 4765-4768.
Rottschäfer, D., Neumann, B., Stammler, H.-G., van Gastel, M., Andrada, D.M., Ghadwal, R.: Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION. 57, 4765-4768 (2018).
Rottschäfer, Dennis, Neumann, Beate, Stammler, Hans-Georg, van Gastel, Maurice, Andrada, Diego M., and Ghadwal, Rajendra. “Crystalline Radicals Derived from Classical N-Heterocyclic Carbenes”. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION 57.17 (2018): 4765-4768.

3 Zitationen in Europe PMC

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