Lecture15outline

Lecture15outline - I Review Peroxy acids react with ketones...

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I. Review • Peroxy acids react with ketones to form tetrahedral intermediates that undergo alkyl group migrations to form esters (Baeyer-Villiger reaction) • For unsymmetrical ketones the migrating group is generally the more substituted group since that group contains a partial positive charge in the transition state • Biological systems perform Bayer-Villiger reactions by using flavin peroxide intermediates that form from the reaction of reduced flavins with O 2 • Imines, compounds that contain a carbon-nitrogen double bond, can be prepared from aldehydes or ketones and primary (one alkyl group) amines • Imines are unstable relative to their constituents, but they can be formed if H 2 O is driven off during their formation • The mechanism of imine formation is similar to oxocarbenium ion formation, though acid is not necessary because of nitrogen's higher nucleophilicitry and lower electronegativity compared to to oxygen • Hydrazones are formed from aldehydes or ketones and hydrazine (or one of its
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Lecture15outline - I Review Peroxy acids react with ketones...

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