Mechanistic Photochemistry of γ-Hydroxy-γ-phenylbutyrophenone. The Nature of the 1,4-Biradical Intermediate

Frederick D. Lewis*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

37 Scopus citations

Abstract

The mechanistic photochemistry of γ-hydroxy-γ-phenylbutyrophenone (1) and its β,γ-dideuterio derivative (2) has been investigated. The presence of a biradical intermediate formed by γ-deuterium abstraction upon photolysis of 2 has been established by the formation of deuterium-hydrogen exchanged ketone 3. A deuterium isotope effect on the rate constant for γ-hydrogen abstraction of 1.7 is observed. A kinetic analysis shows that bond rotations in the biradical are about five times slower than reabstraction of hydrogen or elimination to give acetophenone.

Original languageEnglish (US)
Pages (from-to)5602-5608
Number of pages7
JournalJournal of the American Chemical Society
Volume92
Issue number19
DOIs
StatePublished - Sep 1 1970

ASJC Scopus subject areas

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

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