Electron Apportionment in Cleavage of Radical Anions. 2. Naphthylmethyl Phenyl Ethers vs. Naphthyl Benzyl Ethers

Przemyslaw Maslak, Robert D. Guthrie

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Abstract

Naphthylmethyl phenyl ethers and naphthyl benzyl ethers were found to undergo scission of the H2C-O bond when treated with radical anions of anthracene or fluoranthene. Under comparable conditions, ethers of the naphthylmethyl phenyl series (a and β) reacted more than 104 times faster than ethers of the naphthyl benzyl series (a and β). This preference for regioconservation of spin density in the scission process is interpreted in terms of a-bond polarization at the transition state.

Original languageEnglish (US)
Pages (from-to)2637-2640
Number of pages4
JournalJournal of the American Chemical Society
Volume108
Issue number10
DOIs
Publication statusPublished - Jan 1 1986

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All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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