Le mécanisme de l'hydrolyse acide des aryl‐diazométhanes

In the acid catalysed hydrolysis of three monoaryl‐diazomethanes (p)‐nitrophenyl‐diazométhane (I),p‐chlorophenyl‐diazomethane (II), phenyl‐diazomethane (III), absence of exchange H‐D, solvent isotope effects about 2,6, and general acid catalysis prove that proton transfer is rate determining (A‐SE2 mechanism). Like otherA‐SE2 reactions, the hydrolysis of I is shown to obey theBrønstedcatalysis law with a variety of carboxylic acids; for eight of these acids, αBwas found to be 0,69 ± 0,06.