The alkylation of aromatic hydrocarbons2 and the C-and O-alkylation of phenols3 with olefins in the presence of catalysts such as sulfuric or phosphoric acid lead to the formation of compounds having structures which are in accordance with Markownikoff's rule. The mechanism for these reactions has been described2,30'4 as involving intermediate ester formation between the acid catalyst and the olefin. Posner,6 however, reported that the reaction of thiophenol and olefins in the presence of a mixture of sulfuric acid and acetic acid proceeds abnormally, i. e., contrary to Markownikoff's rule. If Posner's proof of structure, which is open to criticism, is accepted, then one must conclude that either sulfuric acid played no part in the reaction or, what would be less probable, that it formed an intermediate ester of abnormal structure.
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