Measuring the Relative Reactivity of the Carbon-Hydrogen Bonds of Alkanes as Nucleophiles

Olmos Verge, Andrea; Gava, Riccardo; Caballero Bevia, Ana; Pérez Romero, Pedro José

doi:10.1002/anie.201807448

Author

Olmos Verge, Andrea ; Gava, Riccardo; Caballero Bevia, Ana ; Pérez Romero, Pedro José
Publication Date

2018
Publisher

Wiley
Citation

Olmos, A., Gava, R., Noverges, B., Bellezza, D., Jacob, K., Besora, M., Caballero Bevia, A., Pérez Romero, P. J. (2018). Measuring the Relative Reactivity of the Carbon-Hydrogen Bonds of Alkanes as Nucleophiles. Angewandte Chemie International Edition, 57(42), 13848-13852. https://doi.org/10.1002/anie.201807448
Abstract

We report quantitative measurements of the relative reactivities of a series of C-H bonds of gaseous or liquid CnH2n+2 alkanes (n = 1-8, 29 different C-H bonds) towards insitu generated electrophiles (copper, silver, and rhodium carbenes), with methane as the reference. This strategy surpasses the drawback of previous model reactions of alkanes with strong electrophiles suffering from C-C cleavage processes, which precluded direct comparison of the relative reactivities of alkane C-H bonds.
URI

http://hdl.handle.net/10272/15974
Project

info:eu-repo/grantAgreement/MINECO [CTQ2014-52769-C03-01, CTQ2014-52769-C03-02, CTQ2017-82893-C2-1-R, CTQ2014-62234-EXP, CTQ2015-73693-JIN, CTQ2017-87792-R]
info:eu-repo/grantAgreement/Junta de Andalucia [P12-FQM-1765]

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Measuring the Relative Reactivity of the Carbon-Hydrogen Bonds of Alkanes as Nucleophiles

Author

Olmos Verge, Andrea

; Gava, Riccardo; Caballero Bevia, Ana

; Pérez Romero, Pedro José

Publication Date

2018

Publisher

Wiley

Citation

Olmos, A., Gava, R., Noverges, B., Bellezza, D., Jacob, K., Besora, M., Caballero Bevia, A., Pérez Romero, P. J. (2018). Measuring the Relative Reactivity of the Carbon-Hydrogen Bonds of Alkanes as Nucleophiles. Angewandte Chemie International Edition, 57(42), 13848-13852. https://doi.org/10.1002/anie.201807448

Abstract

We report quantitative measurements of the relative reactivities of a series of C-H bonds of gaseous or liquid CnH2n+2 alkanes (n = 1-8, 29 different C-H bonds) towards insitu generated electrophiles (copper, silver, and rhodium carbenes), with methane as the reference. This strategy surpasses the drawback of previous model reactions of alkanes with strong electrophiles suffering from C-C cleavage processes, which precluded direct comparison of the relative reactivities of alkane C-H bonds.

URI

http://hdl.handle.net/10272/15974

Project

info:eu-repo/grantAgreement/MINECO [CTQ2014-52769-C03-01, CTQ2014-52769-C03-02, CTQ2017-82893-C2-1-R, CTQ2014-62234-EXP, CTQ2015-73693-JIN, CTQ2017-87792-R]
info:eu-repo/grantAgreement/Junta de Andalucia [P12-FQM-1765]

Fichero	Tamaño	Formato	Ver	Description
Measuring the relative reactivity.pdf	1.008Mb	PDF	View/Open	versión post-print

Fichero	Tamaño	Formato	Ver	Description
Measuring the relative reactivity.pdf	1.008Mb	PDF	View/Open	versión post-print