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  • Title: Addition of electrophilic and heterocyclic carbon-centered radicals to glyoxylic oxime ethers.
    Author: McNabb SB, Ueda M, Naito T.
    Journal: Org Lett; 2004 Jun 10; 6(12):1911-4. PubMed ID: 15176781.
    Abstract:
    [reaction: see text] Stabilized primary radicals can be formed from alkyl halides in an atom transfer process with Et(3)B. This process depends on the strength of the carbon-halogen bond and the stability of the resulting primary radical. Radicals formed from benzyl iodide and ethyl iodoacetate add to glyoxylic oxime ethers; however, more electrophilic radicals do not. Glyoxylic oxime ethers are also good radical acceptors for heterocyclic carbon-centered secondary radicals, giving novel alpha-amino acid derivatives.
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