The Action of Hydrogen Bromide and Oxygen on Various Ethenoid Compounds. I

Abstract

(1) The reaction of diphenylethylene, atropic acid, and styrene with the mixture of hydrogen bromide and oxygen were studied. In the case of diphenylethylene, diphenylbromomethane, ω-bromoacetophenone, diphenylethylene dibromide, phenol and carbon dioxide were obtained as reaction products. A reaction mechanism was proposed to explain how these compounds were produced. (2) In the case of atropic acid, a large amount of α-hydroxy-β-bromohydratopic acid and a small amount of ω,ω-dibromoaceto phenone and of carbon dioxide were obtained. A consideration on the mechanism of the formation of these products was given on the basis of the identified products and their semiquantitative estimation. (3) Addition of hydrogen bromide to atropic was carried out under various conditions. No reversal of the direction of addition of hydrogen bromide was observed contrary to the previous reference. (4) The reaction of styrene with the mixture of hydrogen bromide and oxygen added an example yielding a phenolic substance ia t...