Photochemistry of Bicycloalkyl Phenyl Ketones

Frederick D. Lewis*, Richard W. Johnson, Ronald A. Rudenlb

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

44 Scopus citations

Abstract

The photochemistry of several bicycloalkyl and cyclopentyl phenyl ketones has been investigated. The quantitative and stereoselective photochemical syntheses of a tricyclo[3.2.1.03′6]octane and tricyclo[3.3.1.02′7]-nonane are described. a-Methyl substituents are found to increase greatly the ratio of photocyclization to photoelimination products and to affect the reactivity of the carbonyl excited state toward 7-hydrogen abstraction. The large variation in the rate constants for secondary 7-hydrogen abstraction (2.5 X 106 to 1 X 1010 sec-1) for the ketones studied is attributed primarily to conformational factors.

Original languageEnglish (US)
Pages (from-to)4292-4297
Number of pages6
JournalJournal of the American Chemical Society
Volume94
Issue number12
DOIs
StatePublished - Jun 1 1972

ASJC Scopus subject areas

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

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