Hydrogen transfer reactions of arenes in molten antimony trichloride

Dworkin, A. S.; Poutsma, Marvin L.; Brynestad, J.; Brown, Lloyd L.; Gilpatrick, L.O.; Smith, G. Pedro

doi:10.1021/ja00512a031

Cited by 18 publications

(8 citation statements)

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“…Therefore, the dominant chloride exchange reaction is BPC1 + A1C13 ---> BP + + A1CI4- [1] Since the A1C13:BPC1 ratio is close to unity for all melts, the liquid may be regarded as consisting of the binary mixture SbC13-25 m/o BP(A1C1D with relatively small additions of A1C13 or BPC1. Since these components vary enormously in chloride donor/acceptor strength, extensive chloride-exchange chemistry occurs on mixing.…”

Section: Resultsmentioning

confidence: 99%

“…For anthracene solutions at the 150 mM concentration level, the extent of reaction was measured by quench and separation at the end of a given reaction period. The same quench and separation procedures were followed as those used previously to study the decomposition of anthracene in SbC13-rich melts at elevated temperatues (1). These solutions contained 160-200 mg of solute.…”

Section: Methodsmentioning

confidence: 99%

“…For this purpose, we chose anthracene as the hydrogen-transfer substrate because of the extensive research (1,(3)(4)(5) on its reactivity in SbC13-rich high-melting mixtures. We felt these mixtures might retain the useful properties of the higher melting salts and, at the same time, have the convenience of being liquid under ambient conditions.…”

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confidence: 99%

“…Studies of polycyclic aromatic hydrocarbons and hydroaromatics in anhydrous SbC13-based melts have shown these melts to be extremely active solventcatalysts for a variety of hydrogen redistribution reactions at surprisingly low temperatures, 80~176 (1)(2)(3)(4)(5). Under certain conditions, these melts can also act as oxidizing reagents toward arenes, and some of the resulting reactions are of unusual types (4,5).…”

mentioning

confidence: 99%

“…Although we made no attempt to establish the solubility limits of those additions, we showed that systems formed by mixing 60 m/o SbCl~, 17-24 rrgo BPC1, and the balance, A1C13, are liquid at 25~ Having established the occurrence of these low-melting SbCl~-rich melts, we wished to determine to what extent SbC13 diluted by 25 m/o BPA1CL at ambient temperature retains the catalytic properties that SbC13 displays at ele-vated temperatures. For this purpose, we chose anthracene as the hydrogen-transfer substrate because of the extensive research (1,(3)(4)(5) on its reactivity in SbC13-rich high-melting mixtures. The results of this investigation are given here.…”

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Reactivity of Anthracene in Liquid SbCl3 ‐ AlCl3 ‐ N ‐ ( 1 ‐ Butyl ) Pyridinium Chloride Mixtures

Zingg

Dworkin

Sørlie

et al. 1984

J. Electrochem. Soc.

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Mixtures of SbC]~ and N-(1-butyl)pyridinium chloride (BPC1) containing 75-87 m]o (mole percent) SbC13 and SbCI~-A1CI~-BPC1 mixtures containing 60 m/o SbCl~ and 16-23 m/o A1CI~ were found to be liquid at 25~ Dilute solutions of anthracene were stable in ternary mixtures containing 18 m/o A1C13, but in mixtures containing 22-24 m/o A1CI~, anthracene reacted under the influence of the solvent, which behaved as both oxidant and H-transfer catalyst. The oxidized product was protonated anthracene, which Was stable in this melt. The source of protons was provided by hydrogen liberating Scholl condensations combined with the reduction of Sb(III). A part of the hydrogen from Scholl reactions reacted with anthracene to form 9,10-dihydroanthracene. By contrast, a liquid mixture without SbC13, A1C13-BPC1 (2:1 mole ratio) proved to be a much less active H-transfer catalyst than the SbCl~-rich liquids even though it is a stronger Lewis acid, and it did not induce protonation beyond a trace attributable to protic impurities. The role of impurities in these mixtures was investigated with results that are relevant to earlier investigations of liquid A1C13-BPC1 mixtures. An improved procedure for purifying BPC1 is described. ) unless CC License in place (see abstract). ecsdl.org/site/terms_use address. Redistribution subject to ECS terms of use (see 138.251.14.35 Downloaded on 2015-03-17 to IP ) unless CC License in place (see abstract). ecsdl.org/site/terms_use address. Redistribution subject to ECS terms of use (see 138.251.14.35 Downloaded on 2015-03-17 to IP ) unless CC License in place (see abstract). ecsdl.org/site/terms_use address. Redistribution subject to ECS terms of use (see 138.251.14.35 Downloaded on 2015-03-17 to IP

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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confidence: 99%

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confidence: 99%

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confidence: 99%

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Reactivity of Anthracene in Liquid SbCl3 ‐ AlCl3 ‐ N ‐ ( 1 ‐ Butyl ) Pyridinium Chloride Mixtures

Zingg

Dworkin

Sørlie

et al. 1984

J. Electrochem. Soc.

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Cu,Ni, andPdMediated Homocoupling Reactions in Biaryl Syntheses: TheUllmann Reaction

Nelson

Crouch

2004

Organic Reactions

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The traditional Ullman reaction is the homocoupling of aromatic halides mediated by copper at elevated temperatures. Ullman first reported this reaction in 1901. Although the coupling conditions first reported are still widely used, a host of modifications have been made to these reactions. Some of these modifications include the use of activated and alternative metals, often resulting in much lower coupling temperatures. Nickel and palladium are the most utilized source of alternative metals, Periodic reviews have been published. This chapter covers the literature on copper, nickel, and palladium mediated homocoupling reactions in biaryl synthesis from 1901 to 2000. The focus of this chapter is the scope and limitation of these processes, preparation of the activated metal, and mechanism of the homocoupling process

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Synthesis of sulfonated polynaphthalene, polyanthracene, and polypyrene as strong solid acids via oxidative coupling polymerization

Toko

Suzuki

Horaguchi

2012

J of Applied Polymer Sci

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Oxidative coupling polymerization of naphthalene, anthracene, and pyrene with FeCl 3 in nitrobenzene under nitrogen gave polynaphthalene (PNP), polyanthracene (PAT), and polypyrene (PPR) in good yields, respectively. PNP, PAT, and PPR were transformed into sulfonated PNP (S-PNP), S-PAT, and S-PPR by the treatment with chlorosulfonic acid in dichloromethane at 25 C for 24 h under nitrogen, respectively. The activities of S-PPR were higher than those of S-PNP and S-PAT. For the hydrolysis of cyclohexyl acetate and oleyl acetate in water, activities of S-PPR, S-PAT, and S-PNP were considerably higher than those of the other conventional solid acids. Rate constants of S-PPR were 2.8 and 11.7 times larger than those of the sulfonated condensed polynuclear aromatic (S-COPNA(PR)) resin (PR ¼ pyrene) for the hydrolysis of cyclohexyl acetate and oleyl acetate, respectively. S-PPR, S-PAT, and S-PNP were reused without significant loss of activities.

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Hydrogen transfer reactions of arenes in molten antimony trichloride

Cited by 18 publications

References 1 publication

Reactivity of Anthracene in Liquid SbCl3 ‐ AlCl3 ‐ N ‐ ( 1 ‐ Butyl ) Pyridinium Chloride Mixtures

Reactivity of Anthracene in Liquid SbCl3 ‐ AlCl3 ‐ N ‐ ( 1 ‐ Butyl ) Pyridinium Chloride Mixtures

Cu,Ni, andPdMediated Homocoupling Reactions in Biaryl Syntheses: TheUllmann Reaction

Synthesis of sulfonated polynaphthalene, polyanthracene, and polypyrene as strong solid acids via oxidative coupling polymerization

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