Measuring the relative reactivity of the carbon–hydrogen bonds of alkanes as nucleophiles - Archive ouverte HAL
Article Dans Une Revue Angewandte Chemie International Edition Année : 2018

Measuring the relative reactivity of the carbon–hydrogen bonds of alkanes as nucleophiles

Résumé

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 in situ 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.

Dates et versions

hal-01953089 , version 1 (12-12-2018)

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Andrea Olmos, Riccardo Gava, Barbara Noverges, Delia Bellezza, Kane Jacob, et al.. Measuring the relative reactivity of the carbon–hydrogen bonds of alkanes as nucleophiles. Angewandte Chemie International Edition, 2018, 57 (42), pp.13848-13852. ⟨10.1002/anie.201807448⟩. ⟨hal-01953089⟩
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