1012-72-2Relevant articles and documents
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Potts,Carpenter
, p. 663 (1939)
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van Tamelen et al.
, p. 6092,6099 (1971)
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Malishev
, p. 883 (1935)
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Kelly,Lee
, p. 757,759 (1955)
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Craig
, p. 195,196 (1935)
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Hennion,Kurtz
, p. 1001 (1943)
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Myhre et al.
, p. 3425 (1966)
Franck,Yanagi
, p. 5814 (1968)
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Grosse,Ipatieff
, (1936)
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Radical aromatic substitution with benzene chromiumtricarbonyl
Byers, Jeffrey H.,Neale, Nathan R.,Bradford Alexander,Gangemi, Stephen P.
, p. 7903 - 7905 (2007)
Radical aromatic substitution of tert-butyl groups for hydrogen on simple arene chromiumtricarbonyl complexes was accomplished. Preexisting tert-butyl groups and methoxy groups directed incoming radicals primarily to the meta-position, and methoxy groups diminished the rate of substitution by roughly tenfold.
TRANSBUTYLATION OF AROMATIC HYDROCARBONS BY 3,6-DI-tert-BUTYLPYROCATECHOL IN PRESENCE OF SULFURIC ACID
Vol'eva, V. B.,Novikova, I. A.,Belostotskaya, I. S.,Komissarova, N. L.,Ershov, V. V.
, p. 1748 - 1750 (1981)
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Bryce-Smith,Owen
, p. 3319,3323 (1960)
Dual Nickel/Photoredox-Catalyzed Deaminative Cross-Coupling of Sterically Hindered Primary Amines
Dorsheimer, Julia R.,Ashley, Melissa A.,Rovis, Tomislav
supporting information, p. 19294 - 19299 (2021/11/23)
We report a method to activate α-3° amines for deaminative arylation via condensation with an electron-rich aldehyde and merge this reactivity with nickel metallaphotoredox to generate benzylic quaternary centers, a common motif in pharmaceuticals and natural products. The reaction is accelerated by added ammonium salts. Evidence is provided in support of two roles for the additive: inhibition of nickel black formation and acceleration of the overall reaction rate. We demonstrate a robust scope of amine and haloarene coupling partners and show an expedited synthesis of ALK2 inhibitors.
Silylium-arene adducts: An experimental and theoretical study
Ibad, Muhammad Farooq,Langer, Peter,Schulz, Axel,Villinger, Alexander
supporting information; experimental part, p. 21016 - 21027 (2012/03/07)
The solvent-coordinated [Me3Si·arene][B(C 6F5)4] salts (arene = benzene, toluene, ethylbenzene, n-propylbenzene, isopropylbenzene, o-xylene, m-xylene, p-xylene, 1,2,3-trimethylbenzene, 1,2,4-trimethylbenzene, 1,3,5-trimethylbenzene) are prepared and fully characterized. As an interesting decomposition product the formation of bissilylated fluoronium ion [Me3Si-F-SiMe 3]+ was observed and even cocrystallized with [Me 3Si·arene][B(C6F5)4] (arene = benzene and toluene). Investigation of the degradation of [Me 3Si·arene][B(C6F5)4] reveals the formation of fluoronium salt [Me3Si-F-SiMe3][B(C 6F5)4], B(C6F5) 3, and a reactive "C6F4" species which could be trapped with CS2. Upon addition of CS2, the formation of a formal S-heterocyclic carbene adduct, C6F 4CS2-B(C6F5)3, was observed. The structure and bonding of substituted [Me3Si· arene][B(C6F5)4] with arene = R nC6H6-n (R = H, Me, Et, Pr, and Bu; n = 0-6) is discussed on the basis of experimental and theoretical data. X-ray data of [Me3Si·arene][B(C6F5)4] salts reveal nonplanar arene species with significant cation...anion interactions. As shown by different theoretical approaches (charge transfer, partial charges, trimethylsilyl affinity values) stabilizing inductive effects occur; however, the magnitude of such effects differs depending on the degree of substitution and the substitution pattern.
Alkylation of pyrocatechol in tert-butyl alcohol-sulfuric acid-benzene
Vol'eva,Prokof'eva,Belostotskaya,Komissarova,Gorbunov,Kurkovskaya
experimental part, p. 1310 - 1312 (2011/12/05)
Alkylation of pyrocatechol with tert-butyl alcohol in benzene in the presence of sulfuric acid gave 3,5-di-tert-butylbenzene-1,2-diol in a higher yield than in analogous reaction with tert-butyl alcohol. This result was rationalized by reduction of inhibitory effect of liberated water, formation of heterogeneous system, and occurrence of the alkylation process in nonpolar organic phase. Intermediate products were identified and found to undergo intra- and intermolecular tert-butyl group transfer with formation of more stable 3,5-di-tert-butylbenzene-1,2-diol. The formation of p-di-tert-butylbenzene indicated participation of benzene in crossalkylation processes. Pleiades Publishing, Ltd., 2011.