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

Ryan Sword, Luke A. Baldwin, John A. Murphy

Research output: Contribution to journalArticle

17 Citations (Scopus)

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.
LanguageEnglish
Pages3560-3570
Number of pages11
JournalOrganic and Biomolecular Chemistry
Volume9
Issue number9
Early online date22 Feb 2011
DOIs
Publication statusPublished - 2011

Fingerprint

Iodides
iodides
fragmentation
Electrons
Substrates
Cations
electrons
Alcohols
halides
alcohols
trapping
cations
4-dimethylaminopyridine
alkoxyl radical

Keywords

  • super-electron-donors
  • SEDs
  • alcohols
  • alkyl radicals
  • heterolytic fragmentation

Cite this

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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.",
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AU - Baldwin, Luke A.

AU - Murphy, John A.

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AB - 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.

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KW - SEDs

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KW - alkyl radicals

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