Electron Apportionment in Cleavage of Radical Anions. 1. Nitro-Substituted Benzyl Phenyl Ethers

Przemyslaw Maslak, Robert D. Guthrie

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Abstract

The radical anions of 4-nitrobenzyl phenyl ethers undergo cleavage at least 104times faster than the radical anions of corresponding 4-nitrophenyl benzyl ethers despite a perceived thermodynamic advantage for the latter set of reactions. It is suggested that this result reflects a kinetic advantage for cleavage reactions which take place with regioconservation of spin density.

Original languageEnglish (US)
Pages (from-to)2628-2636
Number of pages9
JournalJournal of the American Chemical Society
Volume108
Issue number10
DOIs
StatePublished - Jan 1 1986

All Science Journal Classification (ASJC) codes

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

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