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Highly Active Catalysts in Alkene Metathesis: First Observed Transformation of Allenylidene into Indenylidene via Alkenylcarbyne—Ruthenium Species
Author(s) -
Castarlenas Ricardo,
Dixneuf Pierre H.
Publication year - 2003
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200352108
Subject(s) - ruthenium , metathesis , cyclopentene , alkene , chemistry , ring closing metathesis , diene , enyne metathesis , catalysis , cyclooctene , acyclic diene metathesis , protonation , cyclooctadiene , combinatorial chemistry , polymerization , organic chemistry , polymer , ion , natural rubber
A cat. for all seasons : The transformation of the allenylidene‐ruthenium complexes [RuCl(η 6 ‐arene)(CCCR 2 )(PR ${{{\prime \hfill \atop 3\hfill}}}$ )][CF 3 SO 3 ] into indenylidene species [RuCl(η 6 ‐arene)(indenylidene)(PR ${{{\prime \hfill \atop 3\hfill}}}$ )][CF 3 SO 3 ] 2 by the simple protonation with CF 3 SO 3 H and formation of an alkenylcarbyne intermediate (see picture; arene= p ‐cymene) is observed by low temperature NMR experiments. The new in situ generated 18 electron ionic indenylidene species are highly active in the polymerization of cyclooctene and cyclopentene, ring‐closing metathesis of dienes and enynes, and the acyclic diene metathesis of decadiene, thus making it a catalyst for all seasons.