Transalkylation reactions of 4,4'-(1-methylethylidene)bisphenol with diphenyl ether

Wang, Zhi Yuan; Berard, N.; Wisniewska, I.; Hay, Allan S.

doi:10.1021/jo00303a044

Cited by 16 publications

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“…The tert-butyl groups of compound 2 were removed by a trans-tert-butylation reaction with phenol as the tert-butyl acceptor and with methanesulfonic acid as catalyst. 18 To obtain 3 in high yield, oxygen susceptible (easily oxidizable) compound 2 should be transferred to the next step, and the reaction should be run under nitrogen. After all the tertbutyl groups were removed, the product 3 precipitated out from xylene as a much more stable material than the parent compound 2.…”

Section: Resultsmentioning

confidence: 99%

“…The reaction was completed within 3 h. Use of very dry Cs 2 CO 3 is crucial. The tert -butyl groups of compound 2 were removed by a trans- tert -butylation reaction with phenol as the tert -butyl acceptor and with methanesulfonic acid as catalyst . To obtain 3 in high yield, oxygen susceptible (easily oxidizable) compound 2 should be transferred to the next step, and the reaction should be run under nitrogen.…”

Section: Resultsmentioning

confidence: 99%

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Novel Soluble and Fluorescent Poly(arylene ether)s Containing p-Quaterphenyl, 2,5-Bis(4-phenylphenyl)oxadiazole, or 2,5-Bis(4-phenylphenyl)triazole Groups

et al. 2001

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Three novel conjugated biphenols 3, 4, and 8 were synthesized by the Pd(OAc)2-catalyzed regioselective carbon-carbon coupling reaction of 2,6-di-tert-butylphenol or 2-phenylphenol with aryl halides. Although poly(arylene ether)s derived from biphenol 3 and arylene difluorides have low solubility in organic solvents, using 4,4′-(9-fluorenylidene)diphenol or 4,4′-(hexafluoroisopropylidene)diphenol as a comonomer gave soluble poly(arylene ether)s 6a-c. High molecular weight poly(arylene ether)s 7a′-c′ were also prepared from biphenol 4. The biscarbamate-masked monomers 5 and 9 improved the polymerization to give higher molecular weight polymers 7a-e and 10a-e in higher yields. Polymers 7 and 10 possess better film-forming capabilities and are still soluble in organic solvents. Polymers 6, 7, and 10 are all thermally stable with 5% weight loss temperatures higher than 500°C under nitrogen. The polymers show strong blue light emission ranging from 387 to 478 nm in solution, depending on the conjugated structure.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Novel Soluble and Fluorescent Poly(arylene ether)s Containing p-Quaterphenyl, 2,5-Bis(4-phenylphenyl)oxadiazole, or 2,5-Bis(4-phenylphenyl)triazole Groups

et al. 2001

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“…Strategy I was used to obtain the known compounds 3 and 8 − from the acid-mediated condensation of acetone with o -cresol and phenol, respectively. Treatment of 8 with nitric acid (45%) produced the dinitro compounds 5 and 12 and the trinitro derivative 13 as a mixture, from which they were subsequently separated.…”

Section: Resultsmentioning

confidence: 99%

A New Class of HIV-1 Integrase Inhibitors: The 3,3,3‘,3‘-Tetramethyl-1,1‘-spirobi(indan)-5,5‘,6,6‘-tetrol Family

et al. 2000

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Integration is a required step in HIV replication, but as yet no inhibitors of the integration step have been developed for clinical use. Many inhibitors have been identified that are active against purified viral-encoded integrase protein; of these, many contain a catechol moiety. Though this substructure contributes potency in inhibitors, it is associated with toxicity and so the utility of catechol-containing inhibitors has been questioned. We have synthesized and tested a systematic series of derivatives of a catechol-containing inhibitor (1) with the goal of identifying catechol isosteres that support inhibition. We find that different patterns of substitution on the aromatic ring suffice for inhibition when Mn 2+ is used as a cofactor. Importantly, the efficiency is different when Mg 2+ , the more likely in vivo cofactor, is used. These data emphasize the importance of assays with Mg 2+ and offer new catechol isosteres for use in integrase inhibitors.

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“…First published in 1990, Hay’s proposed reaction for the synthesis of the polymer in Figure was only moderately successful: an acid-catalyzed mixture of acetone, phenol, 3,5-dimethylphenol, and diphenylether gave the trimer of the polymer shown in Figure and in 10% yield only. , Nonetheless, a patent quickly followed in 1993 for polymeric species production . Although Hay claimed the polymer of Figure which had a degree of polymerization anywhere from 20 to 100, the polymers in the embodiments of the patent had relatively low glass transition temperatures, ranging from 70 °C seen in his example 9 to a maximum of 93 °C seen in example 10.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of a Regioregular Series of Poly(aryl ether carbonates) and Their Glass Transition Temperatures

Alomar

Boyles

2019

ACS Omega

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Bisphenol A polycarbonate (BPA-PC) is a remarkable high-performance engineering polymer, although it is susceptible to photo-Fries and hydrolytic degradation. New poly(aryl ether carbonates) were synthesized to address these limitations by replacing the chain backbone carbonate ester functionality with aryl ether functionality. The monomers for these new polymers were synthesized by a variation of the Ullmann condensation accelerated by 2,2,6,6-tetramethylheptane-3,5-dione and promoted by Cs2CO3 and 1-methyl-2-pyrrolidinone under mild conditions. Four such bisphenol A-based diarylether monomers containing different mass ratios of carbonate ester groups were prepared and polymerized with phosgene gas to give novel poly(aryl ether carbonates). Polymers were named as di-o-BPA-PC 9′, tri-o-BPA-PC 11′, tetra-o-BPA-PC 13′, and penta-o-BPA-PC 15′ where di-, tri-, tetra-, and penta- reflect the number of diphenylisopropylidene units in each of the respective polymers. The molecular weights of the resulting four poly(aryl ether carbonates) were measured by gel permeation chromatography. Differential scanning calorimetry was used to measure glass transition temperature (Tg). The polymers exhibited weight-average molecular weights up to 4.09 × 105 g/mol and Tg in the range of 136 to 149 °C with no melting temperature peak, indicative of their amorphous character. The new polymers formed transparent and flexible films by solution casting from chloroform solution.

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Transalkylation reactions of 4,4'-(1-methylethylidene)bisphenol with diphenyl ether

Cited by 16 publications

References 0 publications

Novel Soluble and Fluorescent Poly(arylene ether)s Containing p-Quaterphenyl, 2,5-Bis(4-phenylphenyl)oxadiazole, or 2,5-Bis(4-phenylphenyl)triazole Groups

Novel Soluble and Fluorescent Poly(arylene ether)s Containing p-Quaterphenyl, 2,5-Bis(4-phenylphenyl)oxadiazole, or 2,5-Bis(4-phenylphenyl)triazole Groups

A New Class of HIV-1 Integrase Inhibitors: The 3,3,3‘,3‘-Tetramethyl-1,1‘-spirobi(indan)-5,5‘,6,6‘-tetrol Family

Synthesis of a Regioregular Series of Poly(aryl ether carbonates) and Their Glass Transition Temperatures

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