A time-resolved kinetic study of the hydrogen atom transfer (HAT) reactions from secondary alkanamides to the cumyloxyl radical was carried out in acetonitrile. HAT predominantly occurs from the N-alkyl α-C−H bonds, and a >60-fold decrease in kH was observed by increasing the steric hindrance of the acyl and N-alkyl groups. The role of steric and stereoelectronic effects on the reactivity and selectivity is discussed in the framework of HAT reactions from peptides.
Salamone, M., Basili, F., Mele, R., Cianfanelli, M., Bietti, M. (2014). Reactions of the Cumyloxyl Radical with Secondary Amides. The Influence of Steric and Stereoelectronic Effects on the Hydrogen Atom Transfer Reactivity and Selectivity. ORGANIC LETTERS, 16, 6444-6447 [10.1021/ol503277r].
Reactions of the Cumyloxyl Radical with Secondary Amides. The Influence of Steric and Stereoelectronic Effects on the Hydrogen Atom Transfer Reactivity and Selectivity
SALAMONE, MICHELA;BIETTI, MASSIMO
2014-12-04
Abstract
A time-resolved kinetic study of the hydrogen atom transfer (HAT) reactions from secondary alkanamides to the cumyloxyl radical was carried out in acetonitrile. HAT predominantly occurs from the N-alkyl α-C−H bonds, and a >60-fold decrease in kH was observed by increasing the steric hindrance of the acyl and N-alkyl groups. The role of steric and stereoelectronic effects on the reactivity and selectivity is discussed in the framework of HAT reactions from peptides.| File | Dimensione | Formato | |
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