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Carbon-Carbon ?-Bond Formation
1st Edition - January 20, 1992
Editor: G. Pattenden
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Volume 3 covers carbon-to-carbon single bond forming reactions involving sp3, sp2 and sp carbon centers, but only those which do not involve additions to C-X &pgr;-bonds. The… Read more
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Volume 3 covers carbon-to-carbon single bond forming reactions involving sp3, sp2 and sp carbon centers, but only those which do not involve additions to C-X &pgr;-bonds. The volume first compares and contrasts the alkylation reactions of all types of sp3 carbon nucleophiles and also covers vinyl and alkynyl carbanions. Following on from Volume 2, a separate section covers Friedel-Crafts alkylation reactions, which is complemented by discussions of polyene cyclizations and electrophilic transannular cyclizations in synthesis. Coupling reactions leading to &agr;-bond formation, and involving all types of combinations ofsp3, sp2 and sp carbon centers are next covered, including those reactions based on pinacol, acyloin and phenol oxidative coupling reactions, and also the Kolbe reaction. Rearrangement reactions, leading to carbon-to-carbon &agr;-bond formation, are often used in a clever manner in synthesis. The volume includes all those rearrangement reactions based on intermediate carbonium ions and carbanions, and also includes the benzil-benzilic acid and the Wolff rearrangements. The volume closes with coverage of carbonylation reactions, and the use of carbene insertion reactions into the C-H bond in synthesis.
Alkylation of Carbon. Alkylations of enols and enolates. Alkylations of nitrogen-stabilized carbanions. Alkylations of sulphur-and selenium-stabilized carbanions. Alkylations of other heteroatom-stabilized carbanions. Alkylations of nonstabilized carbanions. Alkylations of vinyl carbanions. Alkylations of alkynyl carbanions. Friedel-Crafts alkylations. Polyene cyclizations. Transannular electrophilic cyclizations. Coupling Reactions. Coupling reactions between sp3 carbon centers. Coupling reactions between sp3 and sp2 carbon centers. Coupling reactions between sp2 carbon centers. Coupling reactions between sp2 and sp carbon centers. Coupling reactions between sp carbon centers. Pinacol coupling reactions. Acyloin coupling reactions. Kolbe reactions. Oxidative coupling of phenols and phenol ethers. Rearrangement Reactions. Wagner-Meerwein rearrangements. The Pinacol rearrangement. Acid-catalyzed rearrangements of epoxides. The semipinacol and other rearrangements. Dienone-phenol rearrangements and related reactions. Benzil-benzilic acid rearrangements. The Favorskii rearrangement. The Ramberg-Bäcklund rearrangement. The Wolff rearrangement. The Stevens and related rearrangements. The Wittig rearrangement. Other Carbon-Carbon Bond Forming Reactions. Carbonylation and decarbonylation reactions. Carbon-carbon bond formation by C-H insertion. Author index. Subject index.