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New Indenylidene‐Schiff Base‐Ruthenium Complexes for Cross‐Metathesis and Ring‐Closing Metathesis
Author(s) -
Vila Ana M. Lozano,
Monsaert Stijn,
Drozdzak Renata,
Wolowiec Stanislaw,
Verpoort Francis
Publication year - 2009
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.200900477
Subject(s) - isomerization , ruthenium , chemistry , metathesis , catalysis , ring closing metathesis , salt metathesis reaction , schiff base , grubbs' catalyst , acyclic diene metathesis , photochemistry , combinatorial chemistry , polymer chemistry , organic chemistry , polymerization , polymer
We here report on the stability and catalytic activity of new indenylidene‐Schiff base‐ruthenium complexes 3a – f through representative cross‐metathesis (CM) and ring‐closing metathesis (RCM) reactions. Excellent activity of the new complexes was found for the two selected RCM reactions; prominent conversion was obtained compared to the commercial Hoveyda–Grubbs catalyst 2 . Moreover, excellent results were obtained for a standard CM reaction. Higher conversions were achieved with one of the indenylidene catalysts compared with Hoveyda–Grubbs catalyst. Unexpectedly, an isomerization reaction was observed during the CM reaction of allylbenzene. To the best of our knowledge, isomerization reactions in this model CM reaction in closed systems have never been described using first generation catalysts, including the Hoveyda–Grubbs catalyst. The first model CM reactions as well as the RCM reactions have been monitored using 1 H NMR. The course of the CM reaction of 3‐phenylprop‐1‐ene ( 8 ) and cis ‐1,4‐diacetoxybut‐2‐ene ( 9 ) was monitored by GC. The isomerization reaction was studied by means of GC‐mass spectrometry and in situ IR spectroscopy. All catalysts were structurally characterized by means of 1 H, 13 C, and 31 P NMR spectroscopy.