Under basic conditions (catalytic MeO- in MeOH), compound 1 rearranges through the
Chapter 6, Problem 6.55(choose chapter or problem)
Under basic conditions (catalytic MeO- in MeOH), compound 1 rearranges through the mechanistic sequence shown below to a propellane-type isomer 5 (J. Am. Chem. Soc. 2012, 134, 17877 17880). Note that MeO- is catalytic in that it is consumed in the first step of the mechanism and regenerated in the final step. Provide curved arrows consistent with each mechanistic step and the resonance structure of 2 that is the greatest contributor to the resonance hybrid. O O O O O O O O O O O O MeO H O O O 1 2 5 4 3 Greatest contributing resonance structure of 2 MeO@ @
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