Journal
NEW JOURNAL OF CHEMISTRY
Volume 38, Issue 11, Pages 5382-5390Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c4nj01070a
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Funding
- NSERC
- Michael Smith Foundation for Health Research
- Canada Research Chairs program
- NSERC of Canada
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The conjugate addition of an alcohol to a butynoate ester using an organophosphine catalyst was monitored using pressurized sample infusion electrospray ionization mass spectrometry (PSI-ESI-MS), together with P-31 and H-1 NMR spectroscopy. The combination of methods allowed examination of the reaction progress from the perspective of reactants and products (H-1 NMR) and insights into behaviors of the reaction intermediates and formation of byproducts (P-31 NMR and MS). The resulting traces could be closely approximated through numerical modeling by appropriate selection of rate constants, and a sound understanding of the mechanism and the means by which oligomeric byproducts are formed allows a rational approach to experimental design.
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