Show simple item record

dc.contributor.authorMeng, Xiangtao
dc.contributor.authorRoy Choudhury, Shreya
dc.contributor.authorEdgar, Kevin J.
dc.date.accessioned2017-05-01T06:42:19Z
dc.date.available2017-05-01T06:42:19Z
dc.date.issued2016-04-25
dc.identifierc6py00539j.pdf
dc.identifierc6py00539j1.pdf
dc.identifier.issn1759-9954
dc.identifier.urihttp://hdl.handle.net/10919/77568
dc.description.abstractOlefin cross-metathesis (CM) has been shown to be a versatile, mild, modular, and efficient approach to polysaccharide modification. One issue with regard to this approach is the susceptibility of the initial α,β-unsaturated CM derivatives to H-atom abstraction in the γ-position, followed by radical recombination that leads to insoluble, crosslinked products. In our original approach, we resolved this problem through removing the offending unsaturation by hydrogenation. In the current study, we describe a method to exploit these reactive conjugated olefins, by post-CM thiol-Michael addition, thereby appending additional functionality. CM substrates and thiols bearing various functional groups were combined and reacted, employing amine catalysis. Up to 100% conversion was achieved under proper conditions (e.g. catalyst and reaction time), with minimal side reactions observed. The combination of the two modular reactions creates versatile access to cellulose derivatives equipped with a wide diversity of functional groups.
dc.format.extent3848-3856
dc.format.mimetypeapplication/pdf
dc.language.isoen_US
dc.publisherRoyal Society of Chemistry
dc.relation.ispartofRoyal Society of Chemistry Gold Open Access - 2016
dc.rightsCC BY-NC 3.0
dc.rightsCreative Commons Attribution-NonCommercial 3.0 Unported
dc.rights.urihttps://creativecommons.org/licenses/by-nc/3.0/
dc.titleMultifunctional cellulose esters by olefin cross-metathesis and thiol-Michael addition
dc.typeArticle
dc.rights.holderMeng, Xiangtao
dc.rights.holderRoy Choudhury, Shreya
dc.rights.holderEdgar, Kevin J.
dc.contributor.departmentVirginia Tech. Macromolecules Innovation Institute
dc.contributor.departmentVirginia Tech. Department of Sustainable Biomaterials
dc.contributor.departmentVirginia Tech. Department of Chemistry
dc.title.serialPolymer Chemistry
dc.identifier.doihttps://doi.org/10.1039/c6py00539j
dc.identifier.volume7
dc.identifier.issue23
dc.type.dcmitypeText
dc.type.dcmitypeDataset
dc.identifier.eissn1759-9962


Files in this item

Thumbnail
Thumbnail

This item appears in the following Collection(s)

Show simple item record

CC BY-NC 3.0
License: CC BY-NC 3.0