被撤回的出版物: Homonuclear bond activation using a stable N, N′-diamidocarbene (Retracted article. See vol. 6, pg. 3634, 2015)

The activation of molecules possessing homonuclear bonds (i.e., X-X, where X Br, O, S, or C) using a stable N, N'-diamidocarbene (DAC) is described. Exposing bromine to the DAC at 25 degrees C afforded a substituted tetrahydropyrimidinium salt in good yield (70%). In contrast, treatment of the DAC with benzoyl peroxide or various disulfides afforded the corresponding diamidoketal or diamidothioketal products, respectively, under mild conditions (25 degrees C) and in good yield (60-80%). Mechanistic and kinetic studies of the latter reactions were consistent with a concerted process involving the nucleophilic attack of the DAC on the aforementioned substrates. While the diamidoketal decomposed to the corresponding urea (91% yield) at 25 degrees C, the diamidothioketals produced a thiolate which induced rearrangement to the corresponding ring-opened thioesters (78-90% yield) at elevated temperatures (60 degrees C). The DAC also inserted into the C(O)-C(O) bond of cyclic and acyclic diones as well as the C(O)-CR bond of a cyclopropenone under mild conditions (25-60 degrees C); the corresponding products were subsequently isolated in good yield (75-90%).