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Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes.

The Journal of organic chemistry

Sharma S, Parumala SKR, Peddinti RK.
PMID: 28862850
J Org Chem. 2017 Sep 15;82(18):9367-9383. doi: 10.1021/acs.joc.7b00684. Epub 2017 Sep 01.

A rapid, efficient, and metal-free Lewis acid-mediated methodology has been developed for the site-selective synthesis of unsymmetrical oxygenated biaryls. This simple and efficient methodology furnished highly oxygenated and functionalized unsymmetrical biaryls in good to excellent yields by the direct...

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Sharma S, Parumala SKR, Peddinti RK. Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes. J Org Chem. 2017;82(18):9367-9383doi: 10.1021/acs.joc.7b00684.
Sharma, S., Parumala, S. K. R., & Peddinti, R. K. (2017). Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes. The Journal of organic chemistry, 82(18), 9367-9383. https://doi.org/10.1021/acs.joc.7b00684
Sharma, Shivangi, et al. "Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes." The Journal of organic chemistry vol. 82,18 (2017): 9367-9383. doi: https://doi.org/10.1021/acs.joc.7b00684
Sharma S, Parumala SKR, Peddinti RK. Lewis Acid-Mediated Site-Selective Synthesis of Oxygenated Biaryls from Methoxyphenols and Electron-Rich Arenes. J Org Chem. 2017 Sep 15;82(18):9367-9383. doi: 10.1021/acs.joc.7b00684. Epub 2017 Sep 01. PMID: 28862850.
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Consecutive loss of two benzyl radicals from the [M + Na].

European journal of mass spectrometry (Chichester, England)

Kuck D, Heitkamp S, Letzel M, Ahmed I, Krohn K.
PMID: 29041811
Eur J Mass Spectrom (Chichester). 2018 Feb;24(1):23-32. doi: 10.1177/1469066717729300. Epub 2017 Sep 04.

The electrospray ionization-collision-induced dissociation mass spectra of nine pyrogallol tribenzyl ethers, 2-10, and a catechol dibenzyl ether, 11, that bear various functional groups or larger structural extensions have been studied with respect to the occurrence of a highly characteristic...

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Kuck D, Heitkamp S, Letzel M, et al. Consecutive loss of two benzyl radicals from the [M + Na]. Eur J Mass Spectrom (Chichester). 2017;24(1):23-32doi: 10.1177/1469066717729300.
Kuck, D., Heitkamp, S., Letzel, M., Ahmed, I., & Krohn, K. (2018). Consecutive loss of two benzyl radicals from the [M + Na]. European journal of mass spectrometry (Chichester, England), 24(1), 23-32. https://doi.org/10.1177/1469066717729300
Kuck, Dietmar, et al. "Consecutive loss of two benzyl radicals from the [M + Na]." European journal of mass spectrometry (Chichester, England) vol. 24,1 (2018): 23-32. doi: https://doi.org/10.1177/1469066717729300
Kuck D, Heitkamp S, Letzel M, Ahmed I, Krohn K. Consecutive loss of two benzyl radicals from the [M + Na]. Eur J Mass Spectrom (Chichester). 2018 Feb;24(1):23-32. doi: 10.1177/1469066717729300. Epub 2017 Sep 04. PMID: 29041811.
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Synthesis and properties of unsymmetrical azatrioxa[8]circulenes.

Organic & biomolecular chemistry

Plesner M, Hensel T, Nielsen BE, Kamounah FS, Brock-Nannestad T, Nielsen CB, Tortzen CG, Hammerich O, Pittelkow M.
PMID: 25925233
Org Biomol Chem. 2015 Jun 07;13(21):5937-43. doi: 10.1039/c5ob00676g.

Insights to the subtle reactivity patterns of hydroxy-substituted carbazoles allows the precise synthesis of unsymmetrical azatrioxa[8]circulenes by the reaction of N-benzyl-2,7-di-tert-butyl-3,6-dihydroxycarbazole with two different 1,4-benzoquinones in the presence of an oxidant (chloranil) and a Lewis acid (BF3OEt2). The unique...

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Plesner M, Hensel T, Nielsen BE, et al. Synthesis and properties of unsymmetrical azatrioxa[8]circulenes. Org Biomol Chem. 2015;13(21):5937-43doi: 10.1039/c5ob00676g.
Plesner, M., Hensel, T., Nielsen, B. E., Kamounah, F. S., Brock-Nannestad, T., Nielsen, C. B., Tortzen, C. G., Hammerich, O., & Pittelkow, M. (2015). Synthesis and properties of unsymmetrical azatrioxa[8]circulenes. Organic & biomolecular chemistry, 13(21), 5937-43. https://doi.org/10.1039/c5ob00676g
Plesner, Malene, et al. "Synthesis and properties of unsymmetrical azatrioxa[8]circulenes." Organic & biomolecular chemistry vol. 13,21 (2015): 5937-43. doi: https://doi.org/10.1039/c5ob00676g
Plesner M, Hensel T, Nielsen BE, Kamounah FS, Brock-Nannestad T, Nielsen CB, Tortzen CG, Hammerich O, Pittelkow M. Synthesis and properties of unsymmetrical azatrioxa[8]circulenes. Org Biomol Chem. 2015 Jun 07;13(21):5937-43. doi: 10.1039/c5ob00676g. PMID: 25925233.
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Antibacterial activities and structure-activity relationships of a panel of 48 compounds from Kenyan plants against multidrug resistant phenotypes.

SpringerPlus

Omosa LK, Midiwo JO, Mbaveng AT, Tankeo SB, Seukep JA, Voukeng IK, Dzotam JK, Isemeki J, Derese S, Omolle RA, Efferth T, Kuete V.
PMID: 27386347
Springerplus. 2016 Jun 27;5(1):901. doi: 10.1186/s40064-016-2599-1. eCollection 2016.

In the current study forty eight compounds belonging to anthraquinones, naphthoquinones, benzoquinones, flavonoids (chalcones and polymethoxylated flavones) and diterpenoids (clerodanes and kauranes) were explored for their antimicrobial potential against a panel of sensitive and multi-drug resistant Gram-negative and Gram-positive...

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Omosa LK, Midiwo JO, Mbaveng AT, et al. Antibacterial activities and structure-activity relationships of a panel of 48 compounds from Kenyan plants against multidrug resistant phenotypes. Springerplus. 2016;5(1):901doi: 10.1186/s40064-016-2599-1.
Omosa, L. K., Midiwo, J. O., Mbaveng, A. T., Tankeo, S. B., Seukep, J. A., Voukeng, I. K., Dzotam, J. K., Isemeki, J., Derese, S., Omolle, R. A., Efferth, T., & Kuete, V. (2016). Antibacterial activities and structure-activity relationships of a panel of 48 compounds from Kenyan plants against multidrug resistant phenotypes. SpringerPlus, 5(1), 901. https://doi.org/10.1186/s40064-016-2599-1
Omosa, Leonidah K, et al. "Antibacterial activities and structure-activity relationships of a panel of 48 compounds from Kenyan plants against multidrug resistant phenotypes." SpringerPlus vol. 5,1 (2016): 901. doi: https://doi.org/10.1186/s40064-016-2599-1
Omosa LK, Midiwo JO, Mbaveng AT, Tankeo SB, Seukep JA, Voukeng IK, Dzotam JK, Isemeki J, Derese S, Omolle RA, Efferth T, Kuete V. Antibacterial activities and structure-activity relationships of a panel of 48 compounds from Kenyan plants against multidrug resistant phenotypes. Springerplus. 2016 Jun 27;5(1):901. doi: 10.1186/s40064-016-2599-1. eCollection 2016. PMID: 27386347; PMCID: PMC4923020.
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Control of the Redox Activity of Quantum Dots through Introduction of Fluoroalkanethiolates into Their Ligand Shells.

Journal of the American Chemical Society

Weinberg DJ, He C, Weiss EA.
PMID: 26820492
J Am Chem Soc. 2016 Feb 24;138(7):2319-26. doi: 10.1021/jacs.5b13077. Epub 2016 Feb 11.

Increasing the fraction of 1H,1H,2H,2H-perfluorodecanethiol (PFDT) in the mixed-PFDT/oleate ligand shell of a PbS quantum dot (QD) dramatically reduces the permeability of the ligand shell to alkyl-substituted benzoquinones (s-BQs), as measured by a decrease in the efficiency of collisional...

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Weinberg DJ, He C, Weiss EA. Control of the Redox Activity of Quantum Dots through Introduction of Fluoroalkanethiolates into Their Ligand Shells. J Am Chem Soc. 2016;138(7):2319-26doi: 10.1021/jacs.5b13077.
Weinberg, D. J., He, C., & Weiss, E. A. (2016). Control of the Redox Activity of Quantum Dots through Introduction of Fluoroalkanethiolates into Their Ligand Shells. Journal of the American Chemical Society, 138(7), 2319-26. https://doi.org/10.1021/jacs.5b13077
Weinberg, David J, et al. "Control of the Redox Activity of Quantum Dots through Introduction of Fluoroalkanethiolates into Their Ligand Shells." Journal of the American Chemical Society vol. 138,7 (2016): 2319-26. doi: https://doi.org/10.1021/jacs.5b13077
Weinberg DJ, He C, Weiss EA. Control of the Redox Activity of Quantum Dots through Introduction of Fluoroalkanethiolates into Their Ligand Shells. J Am Chem Soc. 2016 Feb 24;138(7):2319-26. doi: 10.1021/jacs.5b13077. Epub 2016 Feb 11. PMID: 26820492.
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Highly functionalized Bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C(60).

Organic letters

Yen CF, Peddinti RK, Liao CC.
PMID: 10964396
Org Lett. 2000 Sep 07;2(18):2909-12. doi: 10.1021/ol000198s.

[reaction: see text] The Diels-Alder reactions of masked o-benzoquinones (MOBs) with [60]fullerene, affording novel and highly functionalized bicyclo[2.2. 2]octenone-fused [60]fullerene derivatives, are described.

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Yen CF, Peddinti RK, Liao CC. Highly functionalized Bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C(60). Org Lett. 2000;2(18):2909-12doi: 10.1021/ol000198s.
Yen, C. F., Peddinti, R. K., & Liao, C. C. (2000). Highly functionalized Bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C(60). Organic letters, 2(18), 2909-12. https://doi.org/10.1021/ol000198s
Yen, C F, et al. "Highly functionalized Bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C(60)." Organic letters vol. 2,18 (2000): 2909-12. doi: https://doi.org/10.1021/ol000198s
Yen CF, Peddinti RK, Liao CC. Highly functionalized Bicyclo[2.2.2]octenone-fused [60]fullerenes from masked o-benzoquinones and C(60). Org Lett. 2000 Sep 07;2(18):2909-12. doi: 10.1021/ol000198s. PMID: 10964396.
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Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols.

The Journal of organic chemistry

Lai CH, Shen YL, Wang MN, Kameswara Rao NS, Liao CC.
PMID: 12201772
J Org Chem. 2002 Sep 06;67(18):6493-502. doi: 10.1021/jo020171h.

Intermolecular Diels-Alder reactions of masked o-benzoquinones, i.e., 6,6-dimethoxy-2,4-cyclohexadienones 5-7 and 21-24 generated from 2-methoxyphenols 1-3 and 17-20, respectively, with electron-deficient dienophiles leading to highly functionalized bicyclo[2.2.2]octenones are described. The masked o-benzoquinones (MOBs) 5-7 underwent Diels-Alder cycloadditions with methyl acrylate,...

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Lai CH, Shen YL, Wang MN, et al. Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols. J Org Chem. 2002;67(18):6493-502doi: 10.1021/jo020171h.
Lai, C. H., Shen, Y. L., Wang, M. N., Kameswara Rao, N. S., & Liao, C. C. (2002). Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols. The Journal of organic chemistry, 67(18), 6493-502. https://doi.org/10.1021/jo020171h
Lai, Chien-Hsun, et al. "Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols." The Journal of organic chemistry vol. 67,18 (2002): 6493-502. doi: https://doi.org/10.1021/jo020171h
Lai CH, Shen YL, Wang MN, Kameswara Rao NS, Liao CC. Intermolecular Diels-Alder reactions of brominated masked o-benzoquinones with electron-deficient dienophiles. A detour method to synthesize bicyclo[2.2.2]octenones from 2-methoxyphenols. J Org Chem. 2002 Sep 06;67(18):6493-502. doi: 10.1021/jo020171h. PMID: 12201772.
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Mechanism of the Gibbs Reaction. Part 4.(1) Indophenol Formation via N-Chlorobenzoquinone Imine Radical Anions. The Aza-S(RN)2 Chain Reaction Mechanism. Chain Initiation with 1,4-Benzoquinones and Cyanide Ion.

The Journal of organic chemistry

Pallagi I, Toró A, Horváth G.
PMID: 11674654
J Org Chem. 1999 Sep 03;64(18):6530-6540. doi: 10.1021/jo982113v.

The mechanism of the Gibbs reaction, a colorimetric phenol assay that applies N-chlorobenzoquinone imines 1 in an aqueous basic medium, was investigated. It is concluded that N-chloroimine radical anion 7 generated in a single electron transfer (SET) from the...

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Pallagi I, Toró A, Horváth G. Mechanism of the Gibbs Reaction. Part 4.(1) Indophenol Formation via N-Chlorobenzoquinone Imine Radical Anions. The Aza-S(RN)2 Chain Reaction Mechanism. Chain Initiation with 1,4-Benzoquinones and Cyanide Ion. J Org Chem. 1999;64(18):6530-6540doi: 10.1021/jo982113v.
Pallagi, I., Toró, A., & Horváth, G. (1999). Mechanism of the Gibbs Reaction. Part 4.(1) Indophenol Formation via N-Chlorobenzoquinone Imine Radical Anions. The Aza-S(RN)2 Chain Reaction Mechanism. Chain Initiation with 1,4-Benzoquinones and Cyanide Ion. The Journal of organic chemistry, 64(18), 6530-6540. https://doi.org/10.1021/jo982113v
Pallagi, István, et al. "Mechanism of the Gibbs Reaction. Part 4.(1) Indophenol Formation via N-Chlorobenzoquinone Imine Radical Anions. The Aza-S(RN)2 Chain Reaction Mechanism. Chain Initiation with 1,4-Benzoquinones and Cyanide Ion." The Journal of organic chemistry vol. 64,18 (1999): 6530-6540. doi: https://doi.org/10.1021/jo982113v
Pallagi I, Toró A, Horváth G. Mechanism of the Gibbs Reaction. Part 4.(1) Indophenol Formation via N-Chlorobenzoquinone Imine Radical Anions. The Aza-S(RN)2 Chain Reaction Mechanism. Chain Initiation with 1,4-Benzoquinones and Cyanide Ion. J Org Chem. 1999 Sep 03;64(18):6530-6540. doi: 10.1021/jo982113v. PMID: 11674654.
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Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen.

The Journal of organic chemistry

Sakamoto T, Yonehara H, Pac C.
PMID: 11671703
J Org Chem. 1997 May 16;62(10):3194-3199. doi: 10.1021/jo961377j.

The oxidation reactions of hydroquinones, 2-naphthols, or 2,6-di-tert-butylphenol efficiently occurred by catalysis with alumina-supported copper(II) sulfate to give the corresponding benzoquinones, 1,1'-bi-2-naphthols, and 4,4'-diphenoquinone, respectively, in good yields. The synthetic potentiality of the catalytic reactions was demonstrated by easy...

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Sakamoto T, Yonehara H, Pac C. Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen. J Org Chem. 1997;62(10):3194-3199doi: 10.1021/jo961377j.
Sakamoto, T., Yonehara, H., & Pac, C. (1997). Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen. The Journal of organic chemistry, 62(10), 3194-3199. https://doi.org/10.1021/jo961377j
Sakamoto, Takaaki, et al. "Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen." The Journal of organic chemistry vol. 62,10 (1997): 3194-3199. doi: https://doi.org/10.1021/jo961377j
Sakamoto T, Yonehara H, Pac C. Catalytic Activities of CuSO(4)/Al(2)O(3) in Dehydrogenation of Arenes by Dioxygen. J Org Chem. 1997 May 16;62(10):3194-3199. doi: 10.1021/jo961377j. PMID: 11671703.
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Highly diastereoselective and asymmetric Diels-Alder reactions of masked o-benzoquinones with chiral racemic and homochiral furans. Synthesis of optically active tricyclic gamma-lactones.

Organic letters

Chou YY, Peddinti RK, Liao CC.
PMID: 12735740
Org Lett. 2003 May 15;5(10):1637-40. doi: 10.1021/ol034278i.

[reaction: see text] The first examples of highly diastereoselective and asymmetric Diels-Alder cycloadditions of in situ generated masked o-benzoquinones (MOBs) with chiral racemic and homochiral furans bearing a chiral center in the alpha-position leading to highly functionalized diastereomeric/enantioselective tricyclic...

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Chou YY, Peddinti RK, Liao CC. Highly diastereoselective and asymmetric Diels-Alder reactions of masked o-benzoquinones with chiral racemic and homochiral furans. Synthesis of optically active tricyclic gamma-lactones. Org Lett. 2003;5(10):1637-40doi: 10.1021/ol034278i.
Chou, Y. Y., Peddinti, R. K., & Liao, C. C. (2003). Highly diastereoselective and asymmetric Diels-Alder reactions of masked o-benzoquinones with chiral racemic and homochiral furans. Synthesis of optically active tricyclic gamma-lactones. Organic letters, 5(10), 1637-40. https://doi.org/10.1021/ol034278i
Chou, Yu-Yu, et al. "Highly diastereoselective and asymmetric Diels-Alder reactions of masked o-benzoquinones with chiral racemic and homochiral furans. Synthesis of optically active tricyclic gamma-lactones." Organic letters vol. 5,10 (2003): 1637-40. doi: https://doi.org/10.1021/ol034278i
Chou YY, Peddinti RK, Liao CC. Highly diastereoselective and asymmetric Diels-Alder reactions of masked o-benzoquinones with chiral racemic and homochiral furans. Synthesis of optically active tricyclic gamma-lactones. Org Lett. 2003 May 15;5(10):1637-40. doi: 10.1021/ol034278i. PMID: 12735740.
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Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones.

Organic & biomolecular chemistry

Chittimalla SK, Shiao HY, Liao CC.
PMID: 16729136
Org Biomol Chem. 2006 Jun 07;4(11):2267-77. doi: 10.1039/b602928k. Epub 2006 May 04.

A novel and convenient approach, the domino retro Diels-Alder/Diels-Alder reaction sequence for highly stereo- and regioselective synthesis of various bicyclo[2.2.2]octenone and bicyclo[2.2.2]octadienone derivatives is presented. Thus, the masked o-benzoquinones (MOBs) 2a-e generated by the pyrolysis of the respective dimers...

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Chittimalla SK, Shiao HY, Liao CC. Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones. Org Biomol Chem. 2006;4(11):2267-77doi: 10.1039/b602928k.
Chittimalla, S. K., Shiao, H. Y., & Liao, C. C. (2006). Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones. Organic & biomolecular chemistry, 4(11), 2267-77. https://doi.org/10.1039/b602928k
Chittimalla, Santhosh Kumar, et al. "Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones." Organic & biomolecular chemistry vol. 4,11 (2006): 2267-77. doi: https://doi.org/10.1039/b602928k
Chittimalla SK, Shiao HY, Liao CC. Domino retro Diels-Alder/Diels-Alder reaction: an efficient protocol for the synthesis of highly functionalized bicyclo[2.2.2]octenones and bicyclo[2.2.2]octadienones. Org Biomol Chem. 2006 Jun 07;4(11):2267-77. doi: 10.1039/b602928k. Epub 2006 May 04. PMID: 16729136.
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To know the carbon ring; 2,6-polymethylene benzoquinones.

Helvetica chimica acta

PRELOG V, WIESNER K.
PMID: 18915726
Helv Chim Acta. 1948;31(3):870-6. doi: 10.1002/hlca.19480310328.

No abstract available.

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PRELOG V, WIESNER K. Zur Kenntnis des Kohlenstoffringes; 2,6-Polymethylen-benzochinone. To know the carbon ring; 2,6-polymethylene benzoquinones. Helv Chim Acta. 1948;31(3):870-6doi: 10.1002/hlca.19480310328.
PRELOG, V., & WIESNER, K. (1948). Zur Kenntnis des Kohlenstoffringes; 2,6-Polymethylen-benzochinone. To know the carbon ring; 2,6-polymethylene benzoquinones. Helvetica chimica acta, 31(3), 870-6. https://doi.org/10.1002/hlca.19480310328
PRELOG, V, and WIESNER, K. "Zur Kenntnis des Kohlenstoffringes; 2,6-Polymethylen-benzochinone." To know the carbon ring; 2,6-polymethylene benzoquinones. Helvetica chimica acta vol. 31,3 (1948): 870-6. doi: https://doi.org/10.1002/hlca.19480310328
PRELOG V, WIESNER K. Zur Kenntnis des Kohlenstoffringes; 2,6-Polymethylen-benzochinone. To know the carbon ring; 2,6-polymethylene benzoquinones. Helv Chim Acta. 1948;31(3):870-6. doi: 10.1002/hlca.19480310328. German. PMID: 18915726.
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