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dc.contributor.authorFairfull-Smith, KE
dc.contributor.authorJenkins, ID
dc.contributor.authorLoughlin, WA
dc.date.accessioned2017-05-03T11:07:39Z
dc.date.available2017-05-03T11:07:39Z
dc.date.issued2004
dc.date.modified2007-05-02T21:58:20Z
dc.identifier.issn1477-0520
dc.identifier.doi10.1039/B406770C
dc.identifier.urihttp://hdl.handle.net/10072/5734
dc.description.abstractTwo novel dehydrating reagents 3 and 4, based on a phosphonium anhydride and an oxyphosphonium triflate respectively, were prepared by reaction of the corresponding polymer-supported phosphine oxides with triflic anhydride. Reagent 3, based on the novel phosphorus heterocycle 1,1,3,3-tetraphenyl-2-oxa-1,3-diphospholanium bis(trifluoromethanesulfonate), was found to be a useful reagent for ester and amide formation. A wide range ofcoupling/dehydration-type reactions, such as ester, amide, anhydride, peptide, ether and nitrile formation, were performed in high yield using the more readily prepared polymer-supported triphenylphosphine ditriflate 4, which was easily recovered and re-used several times without loss of efficiency. With primary alcohols, both reagents 3 and 4 provide an alternative to the Mitsunobu reaction, where the use of azodicarboxylates and chromatography to remove the phosphine oxide by-product can be avoided. The use of 4-dimethylaminopyridine allowed the esterification of secondary alcohols with 4 to proceed in high yield but with retention of configuration.
dc.description.peerreviewedYes
dc.description.publicationstatusYes
dc.languageEnglish
dc.language.isoeng
dc.publisherThe Royal Society of Chemistry
dc.publisher.placeUK
dc.publisher.urihttp://www.rsc.org/delivery/_ArticleLinking/ArticleLinking.cfm?JournalCode=OB&Year=2004&ManuscriptID=b406770c&Iss=14
dc.relation.ispartofpagefrom1979
dc.relation.ispartofpageto1986
dc.relation.ispartofjournalOrganic and Biomolecular Chemistry.
dc.relation.ispartofvolume2
dc.subject.fieldofresearchMedicinal and biomolecular chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchcode3404
dc.subject.fieldofresearchcode3405
dc.titleNovel polymer-supported coupling/dehydrating reagents for use in organic synthesis
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.rights.copyright© 2004 Royal Society Reproduced in accordance with the copyright policy of the publisher. Use hypertext link for access to the journal's website.
gro.date.issued2004
gro.hasfulltextNo Full Text
gro.griffith.authorJenkins, Ian D.
gro.griffith.authorLoughlin, Wendy A.
gro.griffith.authorFairfull-Smith, Kathryn E.


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