Isocyclic Compounds
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ChemInform Abstract: Use of the Vicinal Element Effect for Regiochemical Control of Quinone Substitutions and Its Implication for Convergent Mitomycin Construction.
First published: 22 May 2010
Abstract
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ChemInform Abstract
Interestingly, the quinones (III) and (IV) undergo preferred substitution of the methoxy group, which is the poorer leaving group. A vicinal element effect is responsible for this observation. Thus, (IV) is found to be a good candidate for the regioselective construction of mitomycins. Starting from the quinone (I), only the undesired regioisomer is formed.
