Perfect switching of photoreactivity by acid: photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate
Mesityl cyclohexanecarboxylate has been photodecarboxylated upon excitation at 254 nm to form cyclohexylmesitylene in good yield in neutral acetonitrile solutions. In the presence of a catalytic amount of the acid and ethanol as a nucleophile, however, the same compound undergoes facile transesterification upon irradiation, affording its ethyl ester in almost quantitative yield.
Mori
T
Department of Molecular Chemistry, Osaka University, 2-1 Yamada-oka, Suita 565-0871, Japan, and Inoue Photochirogenesis Project, ERATO, JST, 4-6-3 Kamishinden, Toyonaka 565-0085, Japan.
Wada
T
Inoue
Y