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Edited By M.F. Semmelhack, Princeton University, NJ, USA
Description Volume 4 focuses on additions and the resulting substitutions at carbon-carbon π-bonds. Part 1 includes processes generally considered
as simple polar reactions, reactive electrophiles and nucleophiles adding to alkenes and alkynes. A major topic is Michael-type addition
to electron deficient π-bonds, featured in the first six chapters. In part 2 are collected the four general processes leading to
nucleophilic aromatic substitution, including radical chain processes and transition metal activation through to π-complexation.
Metal-activated addition (generally by nucleophiles) to alkenes and polyenes is presented in part 3, including allylic alkylation catalyzed
by palladium. The coverage of nonpolar additions in part 4 includes radical additions, organometal addition (Heck reaction), carbene
addition, and 1,3-dipolar cycloadditions.
Contents
Polar Additions to Activated Alkenes and Alkynes. Stabilized nucleophiles with electron deficient alkenes and alkynes.
Conjugate additions of reactive carbanions to activated alkenes and alkynes. Conjugate additions of carbon ligands to activated alkenes
and alkynes mediated by Lewis acids. Organocuprates in the conjugate addition reaction. Asymmetric nucleophilic addition to electron
deficient alkenes. Nucleophilic addition-electrophilic coupling with a carbanion intermediate. Addition of H-X reagents to alkenes and
alkynes. Electrophilic addition of X-Y reagents to alkenes and alkynes. Electrophilic heteroatom cyclizations.
Nucleophilic Aromatic
Substitutions. Arene substitution via nucleophilic addition to electron deficient arenes. Nucleophilic coupling with
aryl radicals. Nucleophilic coupling with arynes. Nucleophilic addition to arene-metal complexes.
Polar Additions to Alkenes
and Alkynes. Heteroatom nucleophiles with metal-activated alkenes and alkynes. Carbon nucleophiles with alkenes and alkynes.
Nucleophiles with allyl-metal complexes. Nucleophiles with cationic pentadienyl-metal complexes. Carbon electrophiles with dienes and
polyenes promoted by transition metals.
Nonpolar Additions to Alkenes and Alkynes. Radical addition reactions. Radical
cyclizations and sequential radical reactions. Vinyl substitutions with organopalladium intermediates. Carbometallation of alkenes and
alkynes. Hydroformylation and related additions of carbon monoxide to alkenes and alkynes. Methylene and nonfunctionalized alkylidene
transfer to form cyclopropanes. Formation and further transformations of 1,1-dihalocyclopropanes. Addition of ketocarbenes to alkenes,
alkynes and aromatic systems. Intermolecular 1,3-dipolar cycloadditions. Intramolecular 1,3-dipolar cycloadditions. Author index. Subject
index.
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