Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification
The synthesis of the novel α,ω-diene 2-(undec-10-en-1-yl)tridec-12-en-1-yl acrylate is described. Thiol-Michael coupling of this substrate followed by chemoselective oxidation of the thioether moiety with triazotriphosphorine tetrachloride (TAPC) furnished a suite of functional and symmetrical ADMET...
| Main Authors: | , , , , |
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| Format: | Journal Article |
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R S C Publications
2014
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| Online Access: | http://hdl.handle.net/20.500.11937/15406 |
| _version_ | 1848748884057128960 |
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| author | van Hensbergen, J. Gaines, T. Wagener, K. Burford, R. Lowe, Andrew |
| author_facet | van Hensbergen, J. Gaines, T. Wagener, K. Burford, R. Lowe, Andrew |
| author_sort | van Hensbergen, J. |
| building | Curtin Institutional Repository |
| collection | Online Access |
| description | The synthesis of the novel α,ω-diene 2-(undec-10-en-1-yl)tridec-12-en-1-yl acrylate is described. Thiol-Michael coupling of this substrate followed by chemoselective oxidation of the thioether moiety with triazotriphosphorine tetrachloride (TAPC) furnished a suite of functional and symmetrical ADMET-active monomers in a quick and convenient manner. Polymerization of these adducts with Grubbs 1st generation catalyst (RuCl2(PCy3)2CHPh) was demonstrated to high conversion, and quantitative radical initiated thiol–ene modification of the backbone C[double bond, length as m-dash]C bonds was performed to impart additional functionality to each ADMET polymer. These reactions highlight the compatibility of thiol-based click chemistries for the preparation and post-modification of functional ADMET materials. |
| first_indexed | 2025-11-14T07:12:08Z |
| format | Journal Article |
| id | curtin-20.500.11937-15406 |
| institution | Curtin University Malaysia |
| institution_category | Local University |
| last_indexed | 2025-11-14T07:12:08Z |
| publishDate | 2014 |
| publisher | R S C Publications |
| recordtype | eprints |
| repository_type | Digital Repository |
| spelling | curtin-20.500.11937-154062017-09-13T13:41:02Z Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification van Hensbergen, J. Gaines, T. Wagener, K. Burford, R. Lowe, Andrew The synthesis of the novel α,ω-diene 2-(undec-10-en-1-yl)tridec-12-en-1-yl acrylate is described. Thiol-Michael coupling of this substrate followed by chemoselective oxidation of the thioether moiety with triazotriphosphorine tetrachloride (TAPC) furnished a suite of functional and symmetrical ADMET-active monomers in a quick and convenient manner. Polymerization of these adducts with Grubbs 1st generation catalyst (RuCl2(PCy3)2CHPh) was demonstrated to high conversion, and quantitative radical initiated thiol–ene modification of the backbone C[double bond, length as m-dash]C bonds was performed to impart additional functionality to each ADMET polymer. These reactions highlight the compatibility of thiol-based click chemistries for the preparation and post-modification of functional ADMET materials. 2014 Journal Article http://hdl.handle.net/20.500.11937/15406 10.1039/c4py00783b R S C Publications restricted |
| spellingShingle | van Hensbergen, J. Gaines, T. Wagener, K. Burford, R. Lowe, Andrew Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification |
| title | Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification |
| title_full | Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification |
| title_fullStr | Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification |
| title_full_unstemmed | Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification |
| title_short | Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification |
| title_sort | functional α,ω-dienes via thiol-michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (admet) polymerization and radical thiol–ene modification |
| url | http://hdl.handle.net/20.500.11937/15406 |