Monitoring ring-closing metathesis: Limitations on the utility of H NMR analysis |
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| Authors: | Sebastien Monfette João A Duarte Silva Eduardo N dos Santos Deryn E Fogg |
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| Institution: | a Center for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, Ottawa, ON, Canada, K1N 6N5
b Departamento de Química - ICEx, Universidade Federal de Minas Gerais, 31270-901 Belo Horizonte, Brazil |
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| Abstract: | The utility and limitations of 1H NMR methods for monitoring the progress of ring-closing metathesis (RCM) reactions are examined. 1H NMR analysis of RCM reactions that yield macrocyclic and medium-ring products can be more problematic than is generally recognized. Interpretation is complicated by the formation of oligomers with an NMR signature identical or closely similar to that of the diene precursor, the RCM target, or a composite of the two. DOSY-NMR can aid in resolving ambiguities in signal assignment, but reliable quantitation requires ancillary methods. |
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| Keywords: | Olefin metathesis Ring-closing metathesis Oligomerization Backbiting 1H NMR DOSY-NMR |
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