J. Am. Chem. Soc.

1951

DOI: 10.1021/ja01153a097

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Condensations by Sodium. XXXI. The Effect of Salts and Other Substances on the Alkylation of Toluene, a Modified Wurtz Reaction¹

Avery A. Morton¹,

Armand E. Brachman²

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Cited by 14 publications

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“…The apparatus and general technique used in this study are the same as are regularly employed (1,2,3,11) in this program of work. The apparatus and general technique used in this study are the same as are regularly employed (1,2,3,11) in this program of work.…”

Section: Methodsmentioning

confidence: 99%

CONDENSATIONS BY SODIUM. XXXVIII. THE METALATION OF tert-BUTYLBENZENE BY AMYLSODIUM AND THE EFFECTS OF ASSOCIATED SALTS^{1, 2}

1955

J. Org. Chem.

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IKTRODUCTIONThis work was intended to be a study of the metalation of the benzene nucleus under the directing influence of an alkyl group which couId not itself be metalated, but steric factors probably limit the scope of polar influence. KO ortho metalation occurs. Only one dimetalation, the m,m', can take place because of the hindrance at the two ortho positions and the failure of sodium to attack a position adjacent to another sodium ion on the ring. Nevertheless some excellent demonstrations of the effects of associated salts, which is one of the special aspects of the work in this laboratory, have been achieved.

“…The apparatus and general technique used in this study are the same as are regularly employed (1,2,3,11) in this program of work. The apparatus and general technique used in this study are the same as are regularly employed (1,2,3,11) in this program of work.…”

Section: Methodsmentioning

confidence: 99%

CONDENSATIONS BY SODIUM. XXXVIII. THE METALATION OF tert-BUTYLBENZENE BY AMYLSODIUM AND THE EFFECTS OF ASSOCIATED SALTS^{1, 2}

1955

J. Org. Chem.

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IKTRODUCTIONThis work was intended to be a study of the metalation of the benzene nucleus under the directing influence of an alkyl group which couId not itself be metalated, but steric factors probably limit the scope of polar influence. KO ortho metalation occurs. Only one dimetalation, the m,m', can take place because of the hindrance at the two ortho positions and the failure of sodium to attack a position adjacent to another sodium ion on the ring. Nevertheless some excellent demonstrations of the effects of associated salts, which is one of the special aspects of the work in this laboratory, have been achieved.

“…In a solvothermal environment, Na pieces can be melted (mp 97.7 °C) and form expanded bubbles, whose breakage yields a large amount of small Na spheres. The Wurtz reaction between Na and TCB occurs on the surface of Na spheres (Scheme a) . With the assistance of formation of NaCl precipitate, intermolecular coupling reaction between TCB molecules proceeds fluently to the right (Scheme S1).…”

Section: Resultsmentioning

confidence: 99%

“…The Wurtz reaction between Na and TCB occurs on the surface of Na spheres (Scheme 1a). 12 With the assistance of formation of NaCl precipitate, intermolecular coupling reaction between TCB molecules proceeds fluently to the right (Scheme S1). Under ideal conditions, 2D PPNs with an ordered structural unit are produced.…”

Section: ■ Materials and Methodsmentioning

confidence: 99%

“…Wurtz reaction is a type of classical coupling reaction for producing samples through inter-and intramolecular dehalogenation. 12 Using polyhalogenated benzene and sodium (or sodium hydride) as the raw materials, polygon carbon, 13 macroporous g-C 3 N 3 , 14 and carbon nanotubes (CNTs) 15 were prepared through solid−vapor Wurtz reactions. Also, heteroatom-substituted carbons 16 and CNT bundles 17 were prepared through solution-based Wurtz reactions.…”

Section: ■ Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Two-Dimensional Polyphenylene Networks with Tunable Micropores for Hydrogen Storage

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et al. 2019

ACS Sustainable Chem. Eng.

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Micropores, especially ultramicropores with pore size smaller than 1 nm, play a crucial role in hydrogen storage. In this contribution, we report on bulk production of two-dimensional (2D) polyphenylene networks (PPNs) through a solution-based Wurtz reaction. A self-assembled mechanism is proposed for the formation of 2D PPNs based on molecular dynamics simulations. The morphology, structure, surface chemistry, and textural properties of the PPNs are greatly influenced by anneal treatment at 450−550 °C in terms of deep thermal dechlorination and cyclodechlorination. The annealed PPNs are featured with moderate specific surface area (S BET ) and wealthy micropores, which can be finely tuned by varying the anneal temperature. For PPNs, there is no direct correlation between the H 2 -uptake capacity and individual textural parameters such as S BET , S micropore , V total pore , V micropore , and V mesopore . The H 2 -uptake capacity is highly dependent on the distribution of ultramicropores and the pore volume of ultramicropores in the range of 0.5−0.8 nm (V ultramicropore 0.5−0.8nm ). The PPNs annealed at 500−520 °C, possessing moderate S BET (459.3−564.9 m 2 g −1 ), relatively high V ultramicropore 0.5−0.8nm , and ultramicropores concentrated at 0.69−0.71 nm, exhibit superior H 2 -storage capacity (4.28−5.39 mmol g −1 ) at 77 K and 1 atm.

“…the respective quantities were 20 and 29%. 6 At -10°and at 0 °instead of 35 0, metalation of phenetole gave 36 and 66 % of o-ethoxybenzoic acid, respectively. Under the same conditions anisóle yielded 42 and 64% of o-anisic acid.…”

Section: Introductionmentioning

confidence: 98%

Condensations by Sodium. XXXV. The Metalation and Cleavage of Ethers, Principally of Alkyl Phenyl Ethers,¹ by Amylsodium and Sodium

1954

J. Am. Chem. Soc.

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Metalationand Cleavage of Ethers by Amylsodium 2973 V with m.p. 312-316°, [o]2Sd +12°, X™,01' 5.59 µ (note similar shift in the infrared lactone band of IV) and broad band at 5.88-5.92 µ; no color with alcoholic ferric chloride. Chromatography of the mother liquors furnished 41 mg. of the keto alcohol II, which was identified as its acetate.

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