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Multiple Rhodium-Catalyzed Cleavages of Single C–C bonds

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journal contribution
posted on 19.02.2016, 17:48 by Christophe Aïssa, Damien Crépin, Daniel J. Tetlow, Kelvin Y. T. Ho
The Rh(I)-catalyzed intramolecular hydroacylation of cis and trans asymmetrically substituted alkylidenecyclobutanes proceeds according to three mechanistic pathways. As shown by deuterium-labeling experiments, the mechanism accounting for the rearrangement of the cis isomers includes the cleavage of three carbon–carbon bonds and a remarkable transannular 3-exo-trig carbometalation.