Journal
SYNLETT
Volume -, Issue 7, Pages 999-1026Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0029-1219790
Keywords
singlet oxygen; ene reaction; kinetic isotope effect; selectivity studies; cyclopropyl probes
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Funding
- Foundation for Education and European Culture
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Singlet oxygen reacts with alkenes, which bear allylic hydrogens, in an ene fashion to afford allylic hydroperoxides. This reaction, apart from its synthetic usefulness, has received extensive mechanistic attention. Numerous experimental studies (e.g., trapping of intermediates, deuterium kinetic isotope effects, regio- or stereoselectivity studies etc.) and to a lesser extend computational work, support a stepwise mechanism with the formation of a three-membered ring (perepoxide-like) intermediate. This Account mainly highlights our group's earlier and recent experimental efforts to ascertain facts relating to this concept.
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