The Photosensitized Oxidation of Strained Olefins

Aryeh A. Frimer

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


The effect of strain in determining the rate, mode and direction of singlet oxygen attack is explored using small ring olefins as substrates. The data suggests that 1O2 is relatively insensitive to strain considerations present in either the starting material or the product. More important factors seem to be the ground state geometry of the olefin, the interatomic distance between the α‐olefinic carbon and the γ‐allylic hydrogen, and the ionization potential of the double bond. Strain does, however, play a crucial and fascinating role in the secondary rearrangements of the primary 1O2 products.

Original languageEnglish
Pages (from-to)194-202
Number of pages9
JournalIsrael Journal of Chemistry
Issue number2-3
StatePublished - 1981


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