Comprehensive organic synthesis : selectivity, strategy [and] efficiency in modern organic chemistry / Vol. 3, Carbon-carbon [sigma]-bond formation / vol. ed. Gerald Pattenden

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. 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 p-bonds. This book compares and contrasts the alkylation reactions of various types of sp3 carbon nucleophiles and also covers vinyl and alkynyl carbanions. The -alkylation of carbonyl compounds by their conversion into nucleophilic enolates or enolate equivalents and subsequent reaction with electrophilic alkylating agents provides one of the main avenues for regio- and stereo-selective formation of carbon-carbon -bonds.