"Experimental and Computational Studies of Nitrenes, Carbenes and Diradicals"

Who: Curt Wentrup

Place: Donostia International Physics Center

Date: Monday, 28 January 2019, 12:00

Several rearrangements of carbenes and nitrenes will be discussed.1 For example, vinylnitrenes can exist as either true nitrenes or 1,3-(1,5)-diradicals, and the ring expansion of arylnitrenes can lead to either cyclic nitrile ylides or cyclic ketenimines.2 Moreover, nitrile imines can exist as carbenes X-C(:)-N=N-Y when electronegative but lone-pair donating substituents X are present,3 and even arylnitrile imines ArCN(+)N(-)H can undergo carbene-like rearrangements. 
Many reactions of these and related types have been elucidated experimentally via matrix isolation spectroscopy (IR and ESR) aided by computational chemistry. 

References
1. Wentrup, C. Carbenes and Nitrenes: Recent Developments in Fundamental Chemistry, Angew. Chem. Int. Ed. 2018, 57, 11508-11521.
2. Wentrup, C.; Kvaskoff, D. Aust. J. Chem., 2013, 66, 286.
3. Bégué, D.; Qiao, G. G.; Wentrup, C. J. Am. Chem. Soc. 2012, 134, 5339; Nunes, C.; Reva, I.; Fausto, R.; Bégué, D.; Wentrup, C. Chem. Commun. 2015, 14712; Bégué, D.; Wentrup, C., et al. J. Org. Chem. 2014, 79, 1418-1426.

Host: Jesus Ugalde

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