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Sander W, Hübert R, Kraka E, et al. 4-Oxo-2,3,5,6-tetrafluorocyclohexa-2,5-dienylidene--a highly electrophilic triplet carbene. Chemistry. 2000;6(24):4567-79doi: 10.1002/1521-3765(20001215)6:24<4567::aid-chem4567>3.0.co;2-a.
Sander, W., Hübert, R., Kraka, E., Gräfenstein, J., & Cremer, D. (2000). 4-Oxo-2,3,5,6-tetrafluorocyclohexa-2,5-dienylidene--a highly electrophilic triplet carbene. Chemistry (Weinheim an der Bergstrasse, Germany), 6(24), 4567-79. https://doi.org/10.1002/1521-3765(20001215)6:24<4567::aid-chem4567>3.0.co;2-a
Sander, W, et al. "4-Oxo-2,3,5,6-tetrafluorocyclohexa-2,5-dienylidene--a highly electrophilic triplet carbene." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 6,24 (2000): 4567-79. doi: https://doi.org/10.1002/1521-3765(20001215)6:24<4567::aid-chem4567>3.0.co;2-a
Sander W, Hübert R, Kraka E, Gräfenstein J, Cremer D. 4-Oxo-2,3,5,6-tetrafluorocyclohexa-2,5-dienylidene--a highly electrophilic triplet carbene. Chemistry. 2000 Dec 15;6(24):4567-79. doi: 10.1002/1521-3765(20001215)6:24<4567::aid-chem4567>3.0.co;2-a. PMID: 11192090.
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Chemistry. 2000 Dec 15;6(24):4567-79. doi: 10.1002/1521-3765(20001215)6:24<4567::aid-chem4567>3.0.co;2-a.

4-Oxo-2,3,5,6-tetrafluorocyclohexa-2,5-dienylidene--a highly electrophilic triplet carbene.

Chemistry (Weinheim an der Bergstrasse, Germany)

W Sander, R Hübert, E Kraka, J Gräfenstein, D Cremer

Affiliations

  1. Lehrstuhl für Organische Chemie II der Ruhr-Universität, Bochum, Germany. [email protected]

PMID: 11192090 DOI: 10.1002/1521-3765(20001215)6:24<4567::aid-chem4567>3.0.co;2-a

Abstract

The 4-oxocyclohexa-2,5-dienylidenes are an interesting class of highly electrophilic carbenes. We investigated the reactivity of the 2,3,5,6-tetrafluorinated and -tetrachlorinated derivatives 1b and 1c with small molecules under conditions of matrix isolation. The reactions with molecular oxygen and with carbon monoxide produce the expected carbonyl O-oxides and ketenes, respectively. As a result of the extreme electrophilicity of 1b and c both carbenes insert with no or very small activation barriers into H2 or the CH bonds of hydrocarbons. Obviously, spin restrictions for these formally spin-forbidden reactions do not result in substantial thermal activation barriers.

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