Additions to C-X ?-Bonds
- S.L. Schreiber, Harvard University, Cambridge, MA, USA
Volume 1 provides a detailed survey of reactions that entail the 1,2-addition of nonstabilized carbanion equivalents of carbonyl, imino and thiocarbonyl functionality. Emphasis has been placed on those reagents that result in highly selective addition reactions. Methods are reported to select, for example, one carbonyl group over another in the same molecule, or to add preferentially a fragment to one (enantiotopic of diastereotopic) face of a carbonyl group. Processes that result from an initial addition to the C=X functional group, for example alkenations and rearrangements, are also covered in this volume.
Published: January 1992
- Nonstabilized Carbanion Equivalents. Carbanions of alkali and alkaline earth cations: (i) synthesis and structural characterization. Carbanions of alkali and alkaline earth cations: (ii) selectivity of carbonyl addition reactions. Organoaluminum reagents. Organocopper reagents. Organo-titanium and organo-zirconium reagents. Organochromium reagents. Organo-zinc, -cadmium and -mercury reagents. Organocerium reagents. Samarium and ytterbium reagents. Lewis acid carbonyl complexation. Lewis acid promoted addition reactions of organometallic compounds. Nucleophilic addition to imines and imine derivatives. Nucleophilic addition to carboxylic acid derivatives. Heteroatom-Stabilized Carbanion Equivalents. Nitrogen stabilization. Boron stabilization. Sulfur stabilization. The Benzoin and related reactions. Silicon stabilization. Selenium stabilization. Transformation of the Carbonyl Group into Nonhydroxylic Groups. Alkene synthesis. Epoxidation and related processes. Skeletal reorganizations: chain extension and ring expansion. Author index. Subject index.