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Lecture10outline - I Review If two substituents on an...

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I. Review • If two substituents on an aromatic ring induce a δ at the same sites, steric interactions control the outcome of the reaction • If the substituents place δ sites at different positions, the better electron donor controls product formation • If the two substituents have approximately the same donor capacity, product formation is difficult to predict • While the ability to predict and control the regiochemistry of electrophilic aromatic substitution reactions, several isomeric patterns are not directly accessible and require multistep syntheses • Direct ortho -selective EAS is difficult, but can be accomplished by introducing a blocking group such as a sulfonic acid or a nitro group at the para -position, leaving the ortho -positions as the only reactive sites – removal of the blocking group provides the ortho -substituted products ortho -Lithiation, in which a basic group guides an organothium reagent to deprotonate the ortho -position, is an approach to yield
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