- Different strategies in electrochemical synthesis of new mono and di-substituted hydroquinone and benzoquinone
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Electrochemical syntheses of 2-indolyl-5-arylsulfonyl-p-benzoquinone derivatives were carried out in two successive oxidation steps. The first involves the oxidation of hydroquinone, 4-(piperazin-1-yl) phenol) and 1-(4-(4-hydroxyphenyl) piperazin-1-yl) et
- Nematollahi, Davood,Momeni, Shima,Khazalpour, Sadegh
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- Green and mild laccase-catalyzed aerobic oxidative coupling of benzenediol derivatives with various sodium benzenesulfinates
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The oxidative coupling reaction between hydroquinone or catechols and various sodium benzenesulfinates was investigated using the laccase from Trametes versicolor, in the presence of O2in a phosphate buffer solution at room temperature to afford sulfonyl benzenediols in 75–95% yield.
- Habibi, Davood,Rahimi, Abdollah,Rostami, Amin,Moradi, Sirvan
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- Electrochemical-In-Situ-Oxidative Sulfonylation of Phenols with Sulfinic Acids as an Access to Sulfonylated Hydroquinones
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The electrochemical in-situ oxidative sulfonylation of phenols with sulfinic acids access to sulfonylated hydroquinones has been developed. A series of sulfonylated hydroquinones were prepared under mild mediator-, catalyst- and exogenous-oxidant-free con
- Sun, Xue,Zhang, Fanjun,Yan, Kelu,Feng, Wenfeng,Sun, Xuejun,Yang, Jianjing,Wen, Jiangwei
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supporting information
p. 3485 - 3490
(2021/06/17)
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- One-pot access to sulfonylated naphthalenediols/hydroquinones from naphthols/phenols with sodium sulfinates in an aqueous medium
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A one-pot method towards sulfonylated hydroquinones/naphthalenediols in an aqueous medium has been developed with up to 97% yield. The whole reaction requiring no transition-metal catalysts could proceed smoothly with hypervalent iodine compounds as the oxidant. Both naphthols and phenols were viable with inexpensive and readily available sodium sulfinates as the sulfonylation reagents under an ambient atmosphere. This procedure is scalable, and the products could be easily obtained without column chromatography isolation. This journal is
- Meng, Lingxin,Zhang, Ruike,Guan, Yuqiu,Chen, Tian,Ding, Zhiqiang,Wang, Gongshu,Reheman, Aikebaier,Chen, Zhangpei,Hu, Jianshe
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supporting information
p. 610 - 614
(2021/01/25)
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- Bisketene Equivalents as Diels-Alder Dienes
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2,5-Bis(tert-butyldimethylsilyloxy)furans are established as vicinal bisketene equivalents for application as dienes in the Diels-Alder reaction. Cycloaddition with olefinic dienophiles, under exceptionally mild conditions, enables convergent access to highly substituted para-hydroquinones in unprotected form via a one-pot Diels-Alder/ring-opening/tautomerization sequence. The synthesis of para-benzoquinones from acetylenic dienophiles, including benzynes, is also demonstrated, and 2,5-bis(tert-butyldimethylsilyloxy)pyrroles are established as competent dienes for the synthesis of para-iminoquinones. Application in natural product synthesis enables gram-scale access to the neuroprotective agent (±)-indanostatin.
- Dissanayake, Isuru,Hart, Jacob D.,Becroft, Emma C.,Sumby, Christopher J.,Newton, Christopher G.
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supporting information
p. 13328 - 13333
(2020/09/03)
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- Ammonium iodide-promoted unprecedented arylsulfonylation of quinone with sodium arylsulfinates
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A novel ammonium iodide-promoted arylsulfonylation of quinones with sodium arylsulfinates has been explored. This reaction proceeded smoothly through unique nucleophilic addition reaction and produced the arylsulfonylation products in moderate to good yields. The reactions proceeded efficiently over a broad range of substrates with good regioselectivity and functional group tolerance.
- Yuan, Jin-Wei,Liu, Shuai-Nan,Qu, Ling-Bo
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p. 6763 - 6772
(2017/10/26)
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- Preparation method for sulfonyl hydroquinone compound
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The invention belongs to the field of organic synthesis, and in particular, relates to a preparation method for a sulfonyl hydroquinone compound. According to the preparation method, a cheap and easily obtained quinone compound is used as a raw material, stable and easy-to-preserve sulfonyl hydrazide is used as a sulfonylation reagent, metal-free catalysis is adopted, reaction conditions are environmentally friendly, the preparation process is simplified, and the yield is increased.
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Paragraph 0065; 0066; 0067
(2017/04/29)
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- Metal-free sulfonylation of quinones with sulfonyl hydrazides in water: Facile access to mono-sulfonylated hydroquinones
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This paper describes a simple and practical protocol for the direct synthesis of monosulfonylated hydroquinones through a transition-metal-free cross-coupling between quinones and sulfonyl hydrazides in water. The procedure tolerates a variety of quinones
- Li, Bin,Li, Yaqin,Yu, Linqian,Wu, Xiaoyu,Wei, Wanguo
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p. 2760 - 2765
(2017/04/14)
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- Synthesis and characterization of a combined main-chain/side-chain liquid-crystalline polymer exhibiting both thermotropic and lyotropic characteristics and its lyotropic phase behavior
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A combined main-chain/side-chain liquid-crystalline polymer (PSHQ4-7CNCOOH), which is composed of poly[(phenylsulfonyl-p-phenylenene 1,4-tetramethylene bis(oxybenzoate)] (PSHQ4) as the main-chain backbone and 8-[(4-cyano-4'-phenyl)oxy]octanoic acid (7CNCO
- Zhou, Ming,Han, Chang Dae
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p. 9602 - 9609
(2008/02/01)
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- Ionic liquids-promoted addition of arylsulfinic acids to p-quinones: A green synthesis of diaryl sulfones
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Arylsulfinic acids undergo smooth conjugate addition to p-quinones in air- and moisture-stable second generation room temperature ionic liquid [bmim]BF4 under mild conditions to produce the corresponding arylsulfonylhydroquinones in excellent yields with high selectivity. In this reaction, ionic liquid plays the dual role as the solvent and the catalyst. The quinones show enhanced reactivity in ionic liquid thereby reducing the reaction times and improving the yields significantly. The presence of ionic liquids helps to avoid the use of either acid or base catalysts for this conversion. The recovered ionic liquid was reused for four to five times with consistent activity.
- Yadav,Reddy,Swamy,Ramireddy
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p. 1849 - 1853
(2007/10/03)
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- Electroorganic Synthesis, 58. Synthesis of Substituted Benzoquinones and their Use for Mediated Electrochemical Conversions
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Hydroxy- (1a-3a) and hydroxyalkyl-substituted benzoquinones (6a-8a, 27a), suited to be immobilized by esterification with polyacrylic acid, are prepared.Their cathodic reduction potential Ep,c (1) correlates linearly with their substituent constant.The cathodic reduction of dioxygen and the palladium(II)-catalyzed anodic oxidation of alkenes are mediated by the benzoquinones 7b, 8b and 27b, respectively. - Key Words: Benzoquinones, substituted / Cyclic voltammetry / Cathodic dioxygen reduction, mediated / Anodic Wacker oxidation, mediated
- Riering, Helmut,Schaefer, Hans J.
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p. 859 - 874
(2007/10/02)
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- Benzoquinones and Related Compounds. Part 6. Addition of Benzenesulfinic Acid to Substituted 1,4-Quinones
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Benzenesulfinic acid adds to 1,4-quinones in the presence of trifluoroacetic acid affording phenylsulfonylhydroquinones.Addition occurs predominantly at the 6-position for methyl-, tert-butyl- and trifluoromethyl-1,4-benzoquinone, but at the 5-position for methoxy-1,4-benzoquinone.Addition to acyl-1,4-benzoquinones occurs exclusively at the 3-position, but under similar conditions phenylsulfonyl-1,4-benzoquinone affords a mixture of 2,3- and 2,6-bisphenylsulfonylhydroquinones, although the former becomes the sole product in the presence of an excess of trifluoraceticacid.These results are rationalised in terms of selective protonation of the quinone.Oxidation of the phenylsulfonylhydroquinones yields the corresponding quinones which with 1,3-dienes give the expected Diels-Alder adducts.
- Bruce, J. Malcolm,Lloyd-Williams, Paul
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p. 2877 - 2884
(2007/10/02)
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- On the Reaction of Methyl and Phenyl Radicals with p-Benzoquinone in Aqueous Solution
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.CH3 and .C6H5 radicals (from the reaction of .OH with dimethyl and diphenyl sulphoxide) react with p-benzoquinone with k (4.5 +/- 1.0) * 1E7 and (1.2 +/- 0.2) * 1E9 dm3 mol-1 s-1, respectively.In both cases an intermediate formation of a transient is observed which could be identified as the unsubstituted semiquinone radical.The molecule and immediate subsequent reaction of these radical adducts with a second p-benzoquinone molecule.The latter process is likely to be an electron transfer.The pulse radiolysis results are supported by steady-state irradiation product analysis.
- Veltwisch, Dieter,Asmus, Klaus-Dieter
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p. 1147 - 1152
(2007/10/02)
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