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Cationation of Dimethylallyl Alcohols by B(C6F5)(3) as Models of the (Re)initiation Reaction in the Bio-Inspired Cationic Polymerization of Isoprene

dc.rights.licenseopen
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorOUARDAD, Samira
hal.structure.identifierResearch Institute for Physical Chemical Problems of the Belarusian State University
hal.structure.identifierInstitut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier [ICGM ICMMM]
dc.contributor.authorKOSTJUK, Sergei V.
hal.structure.identifierInstitut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier [ICGM ICMMM]
dc.contributor.authorGANACHAUD, Francois
hal.structure.identifierUniv Akron, Dept Polymer Sci
hal.structure.identifierUniv Akron, Dept Chem & Biomol Engn
dc.contributor.authorPUSKAS, Judit E.
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
dc.contributor.authorDEFFIEUX, Alain
hal.structure.identifierLaboratoire de Chimie des Polymères Organiques [LCPO]
hal.structure.identifierTeam 1 LCPO : Polymerization Catalyses & Engineering
dc.contributor.authorPERUCH, Frédéric
IDREF: 152900748
dc.date.accessioned2020
dc.date.available2020
dc.date.issued2011
dc.identifier.issn0887-624X
dc.identifier.urihttps://oskar-bordeaux.fr/handle/20.500.12278/20344
dc.description.abstractEnThe polymerization of isoprene initiated by dimethylallyl alcohols (DMAOH) in the presence of Lewis acids (LAs) as coinitiators has been selected as a potential model of the proposed cationic mechanisms involved in natural rubber (NR) biosynthesis. In view to investigate the activation/ionization mechanism of the allyl alcohol chain terminus (PIAllOH), which was shown to exist in NR, different isomers of DMAOH were used as simple models of polyisoprene chain-end structures in the presence of tris(pentafluorophenyl) borane (BLA) as a LA. It is shown that cationation of 3,3-DMAOH by BLA proceeds by direct OH abstraction. However, this process is strongly retarded in the presence of 2,6-di-tert-butylpyridine (d(t)BP), due to the formation of different BLA complexes, one with 3,3-DMAOH, active for cationation, and a dormant one involving its ionized form 3,3-DMAOH. The monomer generated in situ by ionization/proton elimination steps subsequently adds on the primary allylic carbocation form, then resulting in the formation of oligoisoprenes, whereas the tertiary carbocation form of the allylic carbocation yields exclusively to proton elimination and isoprene formation, a possible mechanism of chain-end termination. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 4948-4954, 2011
dc.language.isoen
dc.publisherWiley
dc.subject.encationic polymerization
dc.subject.eninitiators
dc.subject.enNMR
dc.title.enCationation of Dimethylallyl Alcohols by B(C6F5)(3) as Models of the (Re)initiation Reaction in the Bio-Inspired Cationic Polymerization of Isoprene
dc.typeArticle de revue
dc.identifier.doi10.1002/pola.24949
dc.subject.halChimie/Polymères
bordeaux.journalJournal of Polymer Science Part A: Polymer Chemistry
bordeaux.page4948-4954
bordeaux.volume49
bordeaux.hal.laboratoriesLaboratoire de Chimie des Polymères Organiques (LCPO) - UMR 5629*
bordeaux.issue23
bordeaux.institutionBordeaux INP
bordeaux.institutionUniversité de Bordeaux
bordeaux.peerReviewedoui
hal.identifierhal-00956565
hal.version1
hal.origin.linkhttps://hal.archives-ouvertes.fr//hal-00956565v1
bordeaux.COinSctx_ver=Z39.88-2004&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.jtitle=Journal%20of%20Polymer%20Science%20Part%20A:%20Polymer%20Chemistry&rft.date=2011&rft.volume=49&rft.issue=23&rft.spage=4948-4954&rft.epage=4948-4954&rft.eissn=0887-624X&rft.issn=0887-624X&rft.au=OUARDAD,%20Samira&KOSTJUK,%20Sergei%20V.&GANACHAUD,%20Francois&PUSKAS,%20Judit%20E.&DEFFIEUX,%20Alain&rft.genre=article


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