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The Baeyer-Villager Oxidation/Rearrangement O O O O RH O O R1 R2 O R1 R2 O OO O R Criegee intermediate O R1O R2+ O OR Alkyl group that migrates does so with retention of configuration More electron-rich (most substituted) alkyl group migrates in preference Mechanism: RO3H For a review, see: M. Renz, B. Meunier, Eur. J. Org. Chem. 1999, 737.
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Baeyer–Villiger rearrangement. Introducon to radicals Structure; stability. General types of reacZon involving radicals: homolysis, recombinaZon, redox, addiZon, β-scission, subsZtuZon, disproporZonaZon. Problem class relaZng to lectures 1–4. Case studies ElucidaZng mechanisms of rearrangements. Evidence for currently accepted mechanisms ...
- Synopsis
- Types of High Energy Intermediates
- Concerted Rearrangements
- H krel= 350
◼ Carbocations and carbanions NMR spectroscopy and X-ray structures of carbocations; aggregation and pyramidal inversion of carbanions. Reactivity, including SE1, redox, hydride elimination and rearrangements: Wagner–Meerwein, pinacol, semi-pinacol. ◼ Rearrangement of anions and carbocations Orbital theory; Is 3c-2e structure TS or HEI? Stepwise ve...
◼ Electron Deficient Cations Two classes of carbocations reactive towards a) nucleophiles ◼ Electron Rich Anions Carbanion (8 electrons) reactive towards electrophiles acids oxidising agents R • • H H H H • H H H reactive towards electrophiles or nucleophiles other high energy agents oxidising or reducing agents
◼ Neighbouring group participation (NGP) Definition (IUPAC): the direct interaction of the reaction centre(usually, but not necessarily, an incipient carbenium centre) with electrons contained within the parent molecule but not conjugatedwith the reaction centre–could be lone pair, π-bond, or σ-bond A rate increase due to neighbouring group partic...
endo-Ts OTs H racemic rds no NGP O Me OH H AcO OTs rds
1 RearrangementReactions. 1. Rearrangement ReactionsA rearrangement reaction is a board class of organic reactions in which an atom, ion, group of atoms, or chemical unit migrates from one atom to another atom in the same or different species, resulting in a structural isomer o.
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May 1, 2009 · Reaction Scheme • First published 1881 Hofmann, A. W. Chem. Ber. 1881, 14, 2725. Shioiri, T. Comp. Org. Syn. 1991, 6, 800‐806. (Review)
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Benzilic Acid Rearrangement. The benzilic acid rearrangement involves conversion of a 1,2-diketone into a carboxylic acid. The conditions are deceptively simple, hydroxide followed by an acid quench, and lead to the migration of a benzene ring. This mechanism is relatively straightforward.
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The Sommelet-Hauser rearrangement may simply be defined as the rearrangement reaction of certain benzyl quaternary ammonium salts where the reagent used is sodium amide (or alkali amide) and the reaction results in the N,N-dialkylbenzylamine with a new alkyl substituent in the aromatic o-position. Now because the final product is a benzylic ...
