Abstract
AbstractThe title compound 2 was obtained from 1,2‐dimethylenecyclobutane (1) by double addition of dibromocarbene to give the tetrabromide 9, followed by tin hydride reduction to the dibromide 10 and potassium tert‐butoxide elimination of HBr to furnish 2. Silver‐ion‐catalyzed reaction of 2 did not furnish the expected 1,2‐ or 1,4‐ethylene Dewar benzenes 3 and 4, respectively. Instead, in CDCl3 or dioxane, polymeric material was obtained, while in methanol or methanol‐O‐d1, opening of one or both cyclopropene rings and addition of methanol gave 11 or 12E/Z, respectively, depending upon the reaction conditions. The two latter compounds provide valuable information about intermediate 13 in the silver‐ion‐catalyzed rearrangement of bicyclopropenyls to Dewar benzenes. The mechanism of this reaction is discussed.
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