Controlled C-5 methylation of caffeine by benzoyloxy radical addition at C-8

Article abstract of DOI:10.1016/S0040-4039(00)87833-8

C-5 methylation of the model purine compound caffeine by acetyl benzoyl peroxide is the result of preferential addition of the electrophilic benzoyloxy radical at C-8 in neutral medium.X-ray structure and molecular orbital calculations on 1,3,5,7-tetramethyl-5,7-dihydrouric acid are presented.