Acidity measurements in THF. V. Heteroaromatic compounds containing 5-membered rings

Fraser, Robert R.; Mansour, Tarek S.; Savard, Sylvain

doi:10.1139/v85-574

Cited by 96 publications

(99 citation statements)

References 18 publications

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“…In addition, average molecular weight of the polymer determined from GPC (7,l . 10 ) was in good accordance with that from trimethylsilyl and phenyl protons in 'H NMR (7,l . lo'), assuming one trimethylsilyl group per each polymer molecule, indicating the poly(DVB) to have one organosilyl group at the end of polymer chain.…”

Section: A N Anionic Polymerization Of Dvb Initiated With Lithiated Tsupporting

confidence: 79%

Synthesis of Soluble Poly(Divinylbenzene) with an End‐Functional Group

Nagasaki

Kato

et al. 1990

Bulletin des Soc Chimique

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Dedicated to Professor G. Smets on the occasion of his 75th birthday SUMMARY Synthetic methods of end-functional soluble poly(diviny1benzene) [poly DVB)] and A-B-A pe block copolymers having soluble poly(diviny1benzene) segments were investigatedl Lithium N, N'-bi$rimethylsil 1)ethylenediamine was found to initiate an anionic polymerization of 1 ,4-dbinylbenzene (DVB) to form soyuble polymer havin one N,N'-bis trimethy1silyl)ethylenediamine moiety at the end of 01 rner chain almost quantitatively. The potmer was eash y converted to primary-amino-ended soluble pol@dlJ by treating with tetrabutylammonium fluoride. Lithiated trimethylallylsilane also had an initiation ability or DV polymerization. Ween the pol merization was carried out by lithiated trimethylallylsilane, in the presence of diisopropylamine, a soluble pormer was formed. The polymer obtained had one terminal organosilyl group and reactive pendent vinyrgroup in each monomeric unit. A-B-A T e tri block copolymer was synthesized through reactions between primary-amino-ended soluble p o l y ( D 4 anda,o-bis-primary-amino-ended silicone using 4,4'-diphenylmethanediisocyanate as coupling agent. The resulting polymer was a multi-functional polymer having poly(DVB) segments and silicone segments.

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Section: A N Anionic Polymerization Of Dvb Initiated With Lithiated Tsupporting

confidence: 79%

Synthesis of Soluble Poly(Divinylbenzene) with an End‐Functional Group

Nagasaki

Kato

et al. 1990

Bulletin des Soc Chimique

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“…Since the lithiation of N-methylpyrrole 2 (pKa 39.5 [4]) is known to occur preferentially at C-2 under similar conditions, this result shows that the reaction was the simple ring opening by the initially produced lithio-derivative 3, and no isomerization of 3 occurred during the reaction. The exclusive formation of the mono-S-substituted 1,3-propanedithiol 8 was confirmed by gc and GC-MS analyses; i.e., neither the unsubstituted 2,2-diethyl-1,3-propanedithiol 26 nor the S,SЈ-bis-substituted 1,3-propanedithiol was found in the mixture.…”

Section: Resultsmentioning

confidence: 66%

Reaction of a polymerization‐resistant 1,2‐dithiolane with lithiated nitrogen heterocycles

Tazaki¹,

Hieda²,

Maeda³

et al. 1998

Heteroatom Chem.

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“…9 Consequently, lithium amide with organosilyl substituent(s) shows no carbonyl attack under appropriate conditions. 5 Such mild reactivity is one of the reasons why LBA has been extensively utilized for the metalation of complicated materials.…”

Section: Resultsmentioning

confidence: 99%

Lithium Bis(trimethylsilyl)amide Induced Anionic Polymerization of Methyl Methacrylate

Nagasaki

Nishizuka

Tsuruta

1995

Polym J

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KEY WORDSAnionic Polymerization / Methyl Methacrylate / Lithium Bis(trimethylsilyl)amide / Telechelic Oligomer / prim-Amino-ended Poly-(methyl methacrylate) / Lithium-nitrogen-bonded compounds (lithium alkylamides) are known to induce the anionic polymerization of vinyl monomers such as butadiene, 1 isoprene, 2 styrene, 3 and divinylbenzene. 4 This is one way to introduce an amino group at the end of a polymer chain. If lithium alkylamide can be used as an initiator for the anionic polymerization of a,/J-unsaturated esters such as methyl methacrylate (MMA) and methyl acrylate (MA), a new synthetic route for amino-ended poly[(meth)-acrylate ]s can be created.Since the basicity of lithium alkylamide having alkyl substituents such as diisopropylamide (LDA) is too strong, it often induces a carbonyl attack toward such compounds and causes some side reactions. 5 Lithium bis(trimethylsilyl)amide (LBA) is well known as one of the suitable lithiation agents for a-carbonyl protons without carbonyl attack. 6 If LBA is Scheme 1.t To whom correspondence should be addressed. used as the initiator for MMA polymerization, a new route for the synthesis of prim-aminoended PMMA will be available after the hydrolysis of the N-Si bond at the end of the polymer chain. This paper reports the anionic polymerization of MMA initiated with LBA.

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Acidity measurements in THF. V. Heteroaromatic compounds containing 5-membered rings

Cited by 96 publications

References 18 publications

Synthesis of Soluble Poly(Divinylbenzene) with an End‐Functional Group

Synthesis of Soluble Poly(Divinylbenzene) with an End‐Functional Group

Reaction of a polymerization‐resistant 1,2‐dithiolane with lithiated nitrogen heterocycles

Lithium Bis(trimethylsilyl)amide Induced Anionic Polymerization of Methyl Methacrylate

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