The power of solvent in altering the course of photorearrangements

Peter Šebej, Bum Hee Lim, Bong Ser Park, Richard S. Givens, Petr Klán

Research output: Contribution to journalArticlepeer-review

26 Scopus citations

Abstract

A clean bifurcation between two important photochemical reactions through competition of a triplet state Type II H-abstraction reaction with a photo-Favorskii rearrangement for (o/p)-hydroxy-o-methylphenacyl esters that depends on the water content of the solvent has been established. The switch from the anhydrous Type II pathway that yields indanones to the aqueous-dependent pathway producing benzofuranones occurs abruptly at low water concentrations (∼8%). The surprisingly clean yields suggest that such reactions are synthetically promising.

Original languageEnglish
Pages (from-to)644-647
Number of pages4
JournalOrganic Letters
Volume13
Issue number4
DOIs
StatePublished - 18 Feb 2011

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