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Styrene reacts with lead tetra-acetate to give a t least four products, PhCH (0Ac)Et. PhCH (OAc).CH,OAc, PhCH,.CH(OAc),, and PhCHO. The relative yields of the first three are strongly dependent on the conditions of the reaction. A systematic study of these variations, together with kinetic evidence, has shown that the first product results from a radical-chain reaction and the third from a heterolytic process; the 1.2-diacetate is probably formed by t w o concurrent reactions of, respectively, homolytic and heterolytic type.OLEFINS react with lead tetra-acetate to give one or more of a variety of products, depending on the structure of the olefin and the condition~.l-~ These include 1,2-diacetates, enolic and allylic acetates, derivatives of glycollic and glyoxylic acid, and 1 ,l-diacetates whose formation is accompanied by skeletal re-arrangement. Despite this complexity, however, the courses of the reactions are, in almost all cases, satisfactorily accounted for by variants of a basic heterolytic rnechanism.lL3