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Efficient Photodecarboxylation of Trifluoromethyl‐substituted Phenylacetic and Mandelic Acids
Author(s) -
Burns MistyDawn,
Lukeman Matthew
Publication year - 2010
Publication title -
photochemistry and photobiology
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.818
H-Index - 131
eISSN - 1751-1097
pISSN - 0031-8655
DOI - 10.1111/j.1751-1097.2010.00737.x
Subject(s) - chemistry , mandelic acid , phenylacetic acid , trifluoromethyl , quenching (fluorescence) , carbanion , excited state , photochemistry , aqueous solution , organic chemistry , fluorescence , alkyl , physics , nuclear physics , quantum mechanics
A total of eight CF 3 ‐substituted phenylacetic and mandelic acids are shown to undergo efficient photodecarboxylation (PDC; Φ = 0.37–0.74) in basic aqueous solution to give the corresponding trifluoromethyltoluenes or trifluoromethylbenzyl alcohols. The products are consistent with the almost exclusive formation of benzylic carbanions that subsequently react with water, with minor amounts (≤5%) of radical‐derived products detected. Quenching studies indicate that the reaction likely proceeds from the singlet excited state. This work demonstrates that the CF 3 group greatly facilitates the excited state ionic PDC of phenylacetic acids.