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Edited By G. Pattenden, University of Nottingham, UK
Description 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 π-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 α-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 α-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.
Contents
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.
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