Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification
dc.contributor.author | van Hensbergen, J. | |
dc.contributor.author | Gaines, T. | |
dc.contributor.author | Wagener, K. | |
dc.contributor.author | Burford, R. | |
dc.contributor.author | Lowe, Andrew | |
dc.date.accessioned | 2017-01-30T11:49:37Z | |
dc.date.available | 2017-01-30T11:49:37Z | |
dc.date.created | 2015-07-22T20:01:02Z | |
dc.date.issued | 2014 | |
dc.identifier.citation | van Hensbergen, J. and Gaines, T. and Wagener, K. and Burford, R. and Lowe, A. 2014. Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification. Polymer Chemistry. 5 (21): pp. 6225-6235. | |
dc.identifier.uri | http://hdl.handle.net/20.500.11937/15406 | |
dc.identifier.doi | 10.1039/c4py00783b | |
dc.description.abstract |
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. | |
dc.publisher | R S C Publications | |
dc.title | Functional α,ω-dienes via thiol-Michael chemistry: synthesis, oxidative protection, acyclic diene metathesis (ADMET) polymerization and radical thiol–ene modification | |
dc.type | Journal Article | |
dcterms.source.volume | 5 | |
dcterms.source.startPage | 6225 | |
dcterms.source.endPage | 6235 | |
dcterms.source.issn | 1759-9954 | |
dcterms.source.title | Polymer Chemistry | |
curtin.accessStatus | Fulltext not available |