Fragmentations observed in the reactions of a-methoxy-c-alkoxyalkyl iodide substrates with super-electron-donors derived from 4-DMAP and N-methylbenzimidazole

Sword, Ryan and Baldwin, Luke A. and Murphy, John A. (2011) Fragmentations observed in the reactions of a-methoxy-c-alkoxyalkyl iodide substrates with super-electron-donors derived from 4-DMAP and N-methylbenzimidazole. Organic and Biomolecular Chemistry, 9 (9). pp. 3560-3570. ISSN 1477-0520

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Abstract

Reactions of super-electron-donors (SEDs) derived from 4-dimethylaminopyridine and from N-methylbenzimidazole with α-methoxy-γ-alkoxyalkyl iodides lead to liberation of the γ-alkoxy groups as their alcohols. This is consistent with generation of alkyl radicals from the alkyl halide precursors, and trapping of these radicals by the radical-cation of the SED, followed by a heterolytic fragmentation.