Organic Mechanisms - Xiaoping Sun

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of a β‐ketoester via the SN2 reaction of the enolate ...FIGURE 9.27 Alkylation of a diester by reaction of the enolate with 1,4‐dibr...FIGURE 9.28 The intramolecular Claisen condensation of a 1,7‐diester and sub...FIGURE 9.29 (a) The alkoxide base catalyzed crossed Claisen condensation giv...FIGURE 9.30 Structure of acetyl‐coenzyme A.FIGURE 9.31 The enzymatic mechanism for synthesis of citrate, the first step...FIGURE 9.32 Mechanism for thiolase catalyzed Claisen condensation of acetyl‐...

      10 Chapter 10FIGURE 10.1 Major types of rearrangements identified in organic reactions.FIGURE 10.2 The 1,2‐shift in a general carbocation.FIGURE 10.3 The carbocation 1,2‐shifts involved in SbF5 catalyzed isomerizat...FIGURE 10.4 The carbocation rearrangements involved in (a) electrophilic add...FIGURE 10.5 The ring expansions involved in (a) nucleophilic substitution re...FIGURE 10.6 (a) Pinacol rearrangement, (b) acid catalyzed ring‐expansion and...FIGURE 10.7 The concerted cascade carbocation 1,2‐rearrangements in a bioche...FIGURE 10.8 The 1,2‐shift in an epoxide.FIGURE 10.9 Anion‐initiated 1,2‐shifts: (a) Isomerization of a 1,2‐diketone ...FIGURE 10.10 The general mechanism for neighboring leaving group facilitated...FIGURE 10.11 Mechanism of Beckmann rearrangement, a 1,2‐shift in a nitrilium...FIGURE 10.12 Mechanism of Beckmann rearrangement involved in transformation ...FIGURE 10.13 Mechanism of Hofmann rearrangement involved in transformation o...FIGURE 10.14 Mechanism of Hofmann rearrangement for a cyclic amide.FIGURE 10.15 Mechanism of Baeyer–Villiger oxidation (rearrangement): Oxidati...FIGURE 10.16 Mechanism for Baeyer–Villiger oxidation of cyclopentanone to a ...FIGURE 10.17 The regioselectivity for the Baeyer–Villiger oxidation of unsym...FIGURE 10.18 The regio‐ and stereo‐chemistry for the Baeyer–Villiger oxidati...FIGURE 10.19 Mechanism for the acid catalyzed carbon–oxygen rearrangement of...FIGURE 10.20 Electron‐pair facilitated 1,2‐rearrangement in carbene.FIGURE 10.21 Synthesis of carbene from a ketone and stereoelectronic control...FIGURE 10.22 Stereoselective 1,2‐rearrangement of a carbene.FIGURE 10.23 Cyclization of a carbene via a 1,3‐shift.FIGURE 10.24 Photochemical 1,2‐rearrangement of an alkene to a carbene, the ...FIGURE 10.25 Claisen rearrangement (a), an analogous process to the Cope rea...FIGURE 10.26 Claisen rearrangement of a cyclic allyl vinyl ether to a γ,δ‐en...FIGURE 10.27 Claisen rearrangement of trans‐butenyl phenyl ether to an o‐all...FIGURE 10.28 A strong base induced Claisen rearrangement of an allyl ester t...FIGURE 10.29 The Claisen rearrangement of chorismate to prephenate in water ...FIGURE 10.30 The Claisen rearrangement of (a) 6‐β‐glycosylallyl vinyl ether ...FIGURE 10.31 The Claisen rearrangement of a naphthyl ether in water.FIGURE 10.32 Mechanism for the photochemical isomerization of trans‐2‐stilbe...FIGURE 10.33 The photochemical rearrangement of cis‐11‐retinol to its trans‐...FIGURE 10.34 Synthesis of (a) the 6π 5‐organo‐1,3,2,4‐dithiadiazolium hetero...FIGURE 10.35 The photochemical rearrangement of 5‐organo‐1,3,2,4‐dithiadiazo...FIGURE 10.36 Mechanism for the concerted photochemically symmetry allowed bi...

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