Heavy-atom kinetic isotope effects and mechanism of the acid-catalyzed o-semidine and p-semidine rearrangements and disproportionation of 4, 4'- …
ES Rhee, HJ Shine
Index: Rhee, Eun Sook; Shine, Henry J. Journal of the American Chemical Society, 1986 , vol. 108, # 5 p. 1000 - 1006
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Citation Number: 26
Abstract
Abstract: In acidic 60% aqueous dioxane solution at 0" C, 4, 4'-dichlorohydrazobenzene (18) undergoes concurrent disproportionation, to p-chloroaniline (19) and 4, 4'- dichloroazobenzene (20), and 0-(21) and p-semidine (22) rearrangement. In the p-semidine rearrangement one of the chlorine atoms of 18 is displaced, in essence, as C1+. This requires participation of a second molecule of 18 in a redox reaction. The overall fate of 18 ...
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