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Searching for the hidden hydrides : the competition between alkene isomerization and metathesis with Grubbs catalysts

Ashworth, Ian W. and Hillier, Ian H. and Nelson, David J and Percy, Jonathan M and Vincent, Mark A. (2012) Searching for the hidden hydrides : the competition between alkene isomerization and metathesis with Grubbs catalysts. European Journal of Organic Chemistry, 2012 (29). 5673–5677. ISSN 1434-193X

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Abstract

Although Grubbs metathesis catalysts have enabled syntheses of a range of molecules, alkene isomerization, a known and problematic side reaction, is poorly understood. Several mechanisms which have been advanced to account for isomerization were studied by using electronic structure calculations. The pathway catalyzed by a ruthenium hydride emerged as the most facile process by a significant margin. For the first time, we have obtained experimental evidence for the presence of this species in a metathesis-active system.