| Title : Radical cation ester cleavage in solution: mechanism of the mesolytic O-CO bond scission - Schmittel_2001_J.Org.Chem_66_3265 |
| Author(s) : Schmittel M , Peters K , Peters EM , Haeuseler A , Trenkle H |
| Ref : J Org Chem , 66 :3265 , 2001 |
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Abstract :
A wide range of enol carbonate, carbamate, and ester radical cations is characterized in solution by cyclic voltammetry and EPR spectroscopy. Preparative transformations using one-electron oxidants or anodic oxidation yield benzofurans after O-CO bond cleavage. Mechanistic investigations and direct detection of radical intermediates reveal that all enol radical cations undergo exclusively O-CO bond cleavage to provide alpha-carbonyl cations and acyl (or alternatively, alkoxyacyl and aminoacyl) radicals, respectively. The kinetics of the mesolytic fragmentation and the influence of nucleophilic additives have been determined using fast-scan cyclic voltammetry. |
| PubMedSearch : Schmittel_2001_J.Org.Chem_66_3265 |
| PubMedID: 11348106 |
Schmittel M, Peters K, Peters EM, Haeuseler A, Trenkle H (2001)
Radical cation ester cleavage in solution: mechanism of the mesolytic O-CO bond scission
J Org Chem
66 :3265
Schmittel M, Peters K, Peters EM, Haeuseler A, Trenkle H (2001)
J Org Chem
66 :3265