Photolysis of alkoxyacetic acids in the presence of mercury(II) oxide and lodine

Abstract

Homolytic decarboxylation of a series of alkoxyacetic acids has furnished alkoxyalkyl alkoxyacetates when no substituents were present at the 2-position. Electron donating and withdrawing 2-substituents, with the exception of trichloromethyl, afforded products due to fragmentation of the alkoxyacetic acids. The reaction pathway is rationalised on the basis of the reactivity of the alkoxyalkyl iodide intermediates.