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.
@article{mori2000perfect,title={Perfect switching of photoreactivity by acid: Photochemical decarboxylation versus transesterification of mesityl cyclohexanecarboxylate},author={Mori, Tadashi and Wada, Takehiko and Inoue, Yoshihisa},journal={Org. Lett.},volume={2},number={21},pages={3401--3404},year={2000},publisher={ACS Publications},doi={10.1021/ol0065266},url={https://doi.org/10.1021/ol0065266},dimensions={true},tab={paper},}
