Photo-induced Friedel-Crafts Reactions. IV. Indoleacetic Acids

Abstract

The photoreaction of indole with methyl chloroacetate afforded a mixture of seven isomeric methyl indoleacetates, mainly the 4-isomer, whose separation into each component was carried out by repeated column chromatographies. The structues of all of them confirmed by their spectral data and by the unequivocal sysntheses. The unusual reactivity of the 4-position on the indole nucleus was explained on the basis of the calculation data by SCF-CI-MO method.