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  On the Reactivity of Tetrakis(trifluoromethyl)cyclopentadienone towards Carbon-Based Lewis Bases

Holle, S., Escudero, D., Inés, B., Rust, J., Thiel, W., & Alcarazo, M. (2015). On the Reactivity of Tetrakis(trifluoromethyl)cyclopentadienone towards Carbon-Based Lewis Bases. Chemistry – A European Journal, 21(7), 2744-2749. doi:10.1002/chem.201405418.

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chem_201405418_sm_miscellaneous_information.pdf (Supplementary material), 3MB
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chem_201405418_sm_miscellaneous_information.pdf
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Supporting Information
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2015
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Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim
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 Creators:
Holle, Sigrid1, Author           
Escudero, Daniel2, Author           
Inés, Blanca1, Author           
Rust, Jörg3, Author           
Thiel, Walter2, Author           
Alcarazo, Manuel1, Author           
Affiliations:
1Research Group Alcarazo, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445592              
2Research Department Thiel, Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445590              
3Service Department Lehmann (EMR), Max-Planck-Institut für Kohlenforschung, Max Planck Society, ou_1445625              

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Free keywords: density functional calculations; isonitriles; organic Lewis acids; polyfluorinated ketones; zwitterions
 Abstract: The reactivitiy of tetrakis(trifluoromethyl)cyclopentadienone towards different C-based Lewis bases, such as N-heterocyclic carbenes (NHC), ylides and isonitriles, are reported. While sterically not hindered carbenes were found to yield kinetic adducts by regiospecific nucleophilic attack at the position adjacent to the carbonyl group of the ketone, bulkier nucleophiles afforded the thermodynamically more stable O-bridged zwitterions. Interestingly, isonitriles were found to dimerize and trimerize under the same reaction conditions, forming bicyclic products that evolve differently depending on the nature of the substituents.

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Language(s): eng - English
 Dates: 2014-09-262014-12-112015-02-09
 Publication Status: Published in print
 Pages: 6
 Publishing info: -
 Table of Contents: -
 Rev. Type: Peer
 Identifiers: DOI: 10.1002/chem.201405418
 Degree: -

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Title: Chemistry – A European Journal
  Other : Chem. – Eur. J.
  Other : Chem. Eur. J.
Source Genre: Journal
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Publ. Info: Weinheim, Germany : VCH Verlagsgesellschaft
Pages: - Volume / Issue: 21 (7) Sequence Number: - Start / End Page: 2744 - 2749 Identifier: ISSN: 0947-6539
CoNE: https://pure.mpg.de/cone/journals/resource/954926979058