Comprehensive Organic Synthesis: Carbon-Carbon sigma-Bond Formation

Trost B.M., Fleming I., Pattenden G. (eds.)0080405940

Volume 3 covers carbon-to-carbon single bond forming reactions involving sp 3, sp 2 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 sp 3 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 of sp 3, sp 2 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.