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Pure Appl. Chem., 2001, Vol. 73, No. 3, pp. 529-534

Quinone methide intermediates in organic photochemistry

Peter Wan*, Darryl W. Brousmiche, Christy Z. Chen, John Cole, Matthew Lukeman and Musheng Xu

Department of Chemistry, Box 3065, University of Victoria, Victoria, British Columbia, V8W 3V6, Canada

Abstract: Quinone methides are widely encountered reactive intermediates in the chemistry of phenols and related compounds. This paper summarizes our recent progress in uncovering new and general photochemical methods for forming quinone methides of various structural types in aqueous solution. Their mechanism of formation and subsequent chemistry are also discussed. New examples of excited-state intramolecular proton transfer (ESIPT) have been uncovered in these studies. We have also discovered that appropriately designed biphenyls and terphenyls display photochemistry that is best rationalized by highly polarized and planar excited states of these ring systems, which can efficiently lead to the corresponding extended quinone methides.