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The Chemistry of Metallacyclic Alkenylcarbene Complexes, 4 . Unsaturated Metallacyclic Carbene Complexes as Flexible Tools in Organic Synthesis. Novel Rearrangement and Cascade Pathways to Functionalized Alkadienes, Carbo‐, and Heterocycles
Author(s) -
Schobert Rainer
Publication year - 1996
Publication title -
chemische berichte
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.667
H-Index - 136
eISSN - 1099-0682
pISSN - 0009-2940
DOI - 10.1002/cber.19961290602
Subject(s) - chemistry , carbene , nucleophile , cationic polymerization , reactivity (psychology) , ligand (biochemistry) , heteroatom , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , ring (chemistry) , catalysis , receptor , medicine , biochemistry , alternative medicine , pathology
Abstract Cationic metallacyclic carbene complexes of iron and cobalt bearing a terminal η 3 ‐allyl ligand are susceptible to nucleophilic attack at different sites depending on the particular set of substituents, the central metal fragment, and the nucleophile. Attack of enolates, cuprates, acetylides, or heteroatom nucleophiles like phosphanes at the metallacyclic perimeter of the iron complexes 18 provides an easy access to unsaturated organic products like 1,2‐ or 1,3‐dienes, δ‐lactones, and functionalized cyclopentenones through novel rearrangement or cascade pathways. Synthetic applications are described; factors governing reactivity/selectivity are discussed; X‐ray analytical structures of novel metallacycles are provided.