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  Reactions of Cyclopentadienylidenes with CF3I: Electron Bond Donation versus Halogen Bond Donation of the Iodine Atom

Henkel, S., Trosien, I., Mieres-Pérez, J., Lohmiller, T., Savitsky, A., Sanchez-Garcia, E., et al. (2018). Reactions of Cyclopentadienylidenes with CF3I: Electron Bond Donation versus Halogen Bond Donation of the Iodine Atom. The Journal of Organic Chemistry, 83(15), 7586-7592. doi:10.1021/acs.joc.8b01328.

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 Creators:
Henkel, Stefan1, 2, Author
Trosien, Iris1, Author
Mieres-Pérez, Joel1, Author
Lohmiller, Thomas3, Author
Savitsky, Anton3, Author
Sanchez-Garcia, Elsa2, Author              
Sander, Wolfram1, Author
Affiliations:
1Lehrstuhl für Organische Chemie II, Ruhr-Universität Bochum, 44801 Bochum, Germany, ou_persistent22              
2Research Group Sánchez-García, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1950289              
3Max-Planck-Institut für Chemische Energiekonversion, 45470 Mülheim an der Ruhr, Germany, ou_persistent22              

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 Abstract: The interaction of cyclopentadienylidene and tetrachlorocyclopentadienylidene with the halogen bond donor CF3I has been studied by matrix isolation spectroscopy. The carbenes were produced by photolysis of the corresponding diazo compounds, matrix-isolated in argon doped with 1% CF3I at 3 K. Bimolecular reactions between the carbenes and CF3I were induced by annealing these matrices to 25–30 K to allow for the diffusion of trapped species. Instead of classical halogen-bonded complexes, these carbenes form complexes in which the iodine atom is shared between the carbene center and the CF3 group. Photolysis of the complexes at 3 K yields radical pairs, which reversibly react back to the complexes when the matrices are warmed to 25–30 K.

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Language(s): eng - English
 Dates: 2018-05-242018-07-182018-08-03
 Publication Status: Published in print
 Pages: 7
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1021/acs.joc.8b01328
 Degree: -

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Title: The Journal of Organic Chemistry
  Other : J. Org. Chem.
Source Genre: Journal
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Publ. Info: Washington, D.C. : American Chemical Society
Pages: - Volume / Issue: 83 (15) Sequence Number: - Start / End Page: 7586 - 7592 Identifier: ISSN: 0022-3263
CoNE: https://pure.mpg.de/cone/journals/resource/954925416967_1