Oxidation of aryl- and diarylcyclopropanes in a pentasil zeolite: Ring opening with deprotonation or net hydrogen migration

Torsten Herbertz, Prasad Sreeramachandra Lakkaraju, Florian Blume, Matthias Blume, Heinz Dieter Roth

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Abstract

Incorporation of trans-1,2-diphenylcyclopropane (1) and its 3,3-D2- isotopomer into the channels of a redox-active pentasil zeolite (Na-ZSM-5) resulted in the formation of exo,exo-1,3-diphenylallyl radical (2.) and its 2-D1 isotopomer, respectively. This conversion requires oxidation, ring opening, and deprotonation, in an unspecified sequence. The allyl radical 2. is also formed upon incorporation of trans-1,3-diphenylpropene (3). A comparison with the solution photochemistry, in the presence or absence of added base, shows the conversion of 1 into 2. to be a zeolite-specific reaction. Incorporation of arylcyclopropanes 9 (R = H, OCH3) into ZSM-5 generated trans-propenylbenzene radical cations 10.+ (R = H, OCH3); the 2,2-D2 isotopomer of 9 (R = OCH3) gave rise to three different isotopomers of 10.+) (R = OCH3).

Original languageEnglish (US)
Pages (from-to)467-472
Number of pages6
JournalEuropean Journal of Organic Chemistry
Issue number3
DOIs
Publication statusPublished - Feb 2000

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All Science Journal Classification (ASJC) codes

  • Physical and Theoretical Chemistry
  • Organic Chemistry

Keywords

  • Electron transfer
  • Oxidation
  • Radical cations
  • Ring opening
  • Zeolites

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