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The Effects of Triplet Sensitizers' Energies on the Photoreactivity of β,γ‐Unsaturated Methyl Ketones
Author(s) -
Armesto Diego,
Ortiz Maria J.,
Agarrabeitia Antonia R.,
ElBoulifi Noureddin
Publication year - 2005
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200502619
Subject(s) - acetophenone , alkene , chemistry , photochemistry , reactivity (psychology) , triplet state , methane , medicinal chemistry , organic chemistry , molecule , catalysis , medicine , alternative medicine , pathology
Triplet determines reactivity : β,γ‐Unsaturated ketones 1 do not undergo the oxa‐di‐π‐methane (ODPM) rearrangement in the presence of acetophenone or 3 ‐ methoxyacetophenone as a triplet sensitizer. However, they afford the ODPM products 2 when using triplet sensitizers with triplet energies slightly higher than those of the alkene triplets. When the triplet energies of the sensitizers are slightly lower than those of the alkene groups in 1 , ODPM rearrangement occurs along with 1,3‐acyl migration to form enones 3 (see scheme).