A multi-pronged mechanistic study of the phosphine-mediated conjugate addition of an alcohol to an acetylenic ester
| dc.contributor.author | Stoddard, Rhonda L. | |
| dc.contributor.author | Luo, Jingwei | |
| dc.contributor.author | van der Wal, Nicole | |
| dc.contributor.author | O'Rourke, Natasha F. | |
| dc.contributor.author | Wulff, Jeremy E. | |
| dc.contributor.author | McIndoe, J. Scott | |
| dc.date.accessioned | 2018-09-14T23:13:13Z | |
| dc.date.available | 2018-09-14T23:13:13Z | |
| dc.date.copyright | 2014 | en_US |
| dc.date.issued | 2014 | |
| dc.description.abstract | 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 31P and 1H NMR spectroscopy. The combination of methods allowed examination of the reaction progress from the perspective of reactants and products (1H NMR) and insights into behaviors of the reaction intermediates and formation of byproducts (31P 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. | en_US |
| dc.description.reviewstatus | Reviewed | en_US |
| dc.description.scholarlevel | Faculty | en_US |
| dc.description.sponsorship | JSM thanks NSERC (Discovery and Discovery Accelerator Supplements) for operational and infrastructural support. NvdW thanks NSERC for an Undergraduate Summer Research Award. JEW thanks the Michael Smith Foundation for Health Research and the Canada Research Chairs program for salary support, and NSERC of Canada for operational funds. RLS thanks Chris Barr and Dr Ori Granot for invaluable advice and assistance with NMR and PSI-ESI-MS. NFO thanks NSERC for a fellowship. | en_US |
| dc.identifier.citation | Stoddard, R.L., Luo,J., van der Wal, N., O’Rourke, N.F., Wulff, J.E. & McIndoe, J.S. (2014). A multi-pronged mechanistic study of the phosphine-mediated conjugate addition of an alcohol to an acetylenic ester. New Journal of Chemistry, 38, 5382- 5390. https://doi.org/10.1039/c4nj01070a | en_US |
| dc.identifier.uri | https://doi.org/10.1039/c4nj01070a | |
| dc.identifier.uri | http://hdl.handle.net/1828/10072 | |
| dc.language.iso | en | en_US |
| dc.publisher | New Journal of Chemistry | en_US |
| dc.title | A multi-pronged mechanistic study of the phosphine-mediated conjugate addition of an alcohol to an acetylenic ester | en_US |
| dc.type | Article | en_US |