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Synthesis of mercaptopropyl-(phenylene)s-benzoates passivated gold nanoparticles: Implications for plasmonic photovoltaic cells.

Journal of colloid and interface science

de León A, Arias E, Moggio I, Gallardo-Vega C, Ziolo R, Rodríguez O, Trigari S, Giorgetti E, Leibig C, Evans D.
PMID: 26122799
J Colloid Interface Sci. 2015 Oct 15;456:182-9. doi: 10.1016/j.jcis.2015.06.029. Epub 2015 Jun 23.

UNLABELLED: The incorporation of gold nanoparticles in heterojunction solar cells is expected to increase the efficiency due to plasmon effects, but the literature studies are sometimes controversial. In this work, gold nanoparticles passivated with (Ph)n-(CH2)3SH (n=1, 2, 3) have...

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de León A, Arias E, Moggio I, et al. Synthesis of mercaptopropyl-(phenylene)s-benzoates passivated gold nanoparticles: Implications for plasmonic photovoltaic cells. J Colloid Interface Sci. 2015;456:182-9doi: 10.1016/j.jcis.2015.06.029.
de León, A., Arias, E., Moggio, I., Gallardo-Vega, C., Ziolo, R., Rodríguez, O., Trigari, S., Giorgetti, E., Leibig, C., & Evans, D. (2015). Synthesis of mercaptopropyl-(phenylene)s-benzoates passivated gold nanoparticles: Implications for plasmonic photovoltaic cells. Journal of colloid and interface science, 456182-9. https://doi.org/10.1016/j.jcis.2015.06.029
de León, Arxel, et al. "Synthesis of mercaptopropyl-(phenylene)s-benzoates passivated gold nanoparticles: Implications for plasmonic photovoltaic cells." Journal of colloid and interface science vol. 456 (2015): 182-9. doi: https://doi.org/10.1016/j.jcis.2015.06.029
de León A, Arias E, Moggio I, Gallardo-Vega C, Ziolo R, Rodríguez O, Trigari S, Giorgetti E, Leibig C, Evans D. Synthesis of mercaptopropyl-(phenylene)s-benzoates passivated gold nanoparticles: Implications for plasmonic photovoltaic cells. J Colloid Interface Sci. 2015 Oct 15;456:182-9. doi: 10.1016/j.jcis.2015.06.029. Epub 2015 Jun 23. PMID: 26122799.
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Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines.

The Journal of organic chemistry

Schmidt A, Batsyts S, Smeyanov A, Freese T, Hübner EG, Nieger M.
PMID: 27088664
J Org Chem. 2016 May 20;81(10):4202-9. doi: 10.1021/acs.joc.6b00561. Epub 2016 Apr 28.

3-Ethynylquinoline was subjected to a Sonogashira-Hagihara reaction with methyl 2-, 3-, and 4-bromobenzoates, respectively, and then N-methylated to give 3-[((methoxycarbonyl)phenyl)ethynyl]-1-methylquinolinium salts (two X-ray analyses). On saponification of the 3- and 4-substituted benzoates, the mesomeric betaines 3- and 4-[(1-methylquinolinium-3-yl)ethynyl]benzoates were...

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Schmidt A, Batsyts S, Smeyanov A, et al. Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines. J Org Chem. 2016;81(10):4202-9doi: 10.1021/acs.joc.6b00561.
Schmidt, A., Batsyts, S., Smeyanov, A., Freese, T., Hübner, E. G., & Nieger, M. (2016). Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines. The Journal of organic chemistry, 81(10), 4202-9. https://doi.org/10.1021/acs.joc.6b00561
Schmidt, Andreas, et al. "Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines." The Journal of organic chemistry vol. 81,10 (2016): 4202-9. doi: https://doi.org/10.1021/acs.joc.6b00561
Schmidt A, Batsyts S, Smeyanov A, Freese T, Hübner EG, Nieger M. Dipolar Bent and Linear Acetylenes Substituted by Cationic Quinolinium and Anionic Benzoates. Formation of Mesomeric Betaines. J Org Chem. 2016 May 20;81(10):4202-9. doi: 10.1021/acs.joc.6b00561. Epub 2016 Apr 28. PMID: 27088664.
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Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles.

Chemistry, an Asian journal

Tan JK, Mathiew M, Nayak S, Chan PWH.
PMID: 28608646
Chem Asian J. 2017 Jul 04;12(13):1475-1479. doi: 10.1002/asia.201700419. Epub 2017 Jun 13.

A synthetic method for the efficient assembly of benzo[c]carbazole derivatives that relies on silica gel-activated benzoic acid-mediated cycloaromatization of 1H-indol-2-yl propargyl benzoates under atmospheric conditions is described. Robust with a variety of substitution patterns tolerated, the reaction provides a...

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Tan JK, Mathiew M, Nayak S, et al. Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chem Asian J. 2017;12(13):1475-1479doi: 10.1002/asia.201700419.
Tan, J. K., Mathiew, M., Nayak, S., & Chan, P. W. H. (2017). Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chemistry, an Asian journal, 12(13), 1475-1479. https://doi.org/10.1002/asia.201700419
Tan, Javey Khiapeng, et al. "Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles." Chemistry, an Asian journal vol. 12,13 (2017): 1475-1479. doi: https://doi.org/10.1002/asia.201700419
Tan JK, Mathiew M, Nayak S, Chan PWH. Brønsted Acid-Mediated Cycloaromatization of 1H-Indol-2-yl Propargyl Benzoates to 7H-Benzo[c]carbazoles. Chem Asian J. 2017 Jul 04;12(13):1475-1479. doi: 10.1002/asia.201700419. Epub 2017 Jun 13. PMID: 28608646.
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Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates.

Organic chemistry frontiers : an international journal of organic chemistry

Crawford JM, Shelton KE, Reeves EK, Sadarananda BK, Kalyani D.
PMID: 26478819
Org Chem Front. 2015 Jun 01;2(6):726-729. doi: 10.1039/C5QO00040H. Epub 2015 May 12.

This manuscript describes a Ni-catalyzed method for the direct arylation of azoles using benzoates. Perfluorophenyl and 2-nitrobenzoates participate in these reactions to afford the corresponding products in modest to good yields. The efficiency of the arylations with perfluorobenzoates is...

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Crawford JM, Shelton KE, Reeves EK, et al. Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates. Org Chem Front. 2015;2(6):726-729doi: 10.1039/C5QO00040H.
Crawford, J. M., Shelton, K. E., Reeves, E. K., Sadarananda, B. K., & Kalyani, D. (2015). Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates. Organic chemistry frontiers : an international journal of organic chemistry, 2(6), 726-729. https://doi.org/10.1039/C5QO00040H
Crawford, Jennifer M, et al. "Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates." Organic chemistry frontiers : an international journal of organic chemistry vol. 2,6 (2015): 726-729. doi: https://doi.org/10.1039/C5QO00040H
Crawford JM, Shelton KE, Reeves EK, Sadarananda BK, Kalyani D. Nickel-Catalyzed Decarboxylative Arylation of Azoles with Perfluoro- and Nitrobenzoates. Org Chem Front. 2015 Jun 01;2(6):726-729. doi: 10.1039/C5QO00040H. Epub 2015 May 12. PMID: 26478819; PMCID: PMC4606873.
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Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation.

European journal of organic chemistry

Rackl D, Kais V, Lutsker E, Reiser AO.
PMID: 28529446
European J Org Chem. 2017 Apr 18;2017(15):2130-2138. doi: 10.1002/ejoc.201700014. Epub 2017 Feb 28.

The synthesis of chiral tetrahydrofurans and pyrrolidines starting from 1,2-diols or β-amino alcohols, respectively, by visible-light-mediated deoxygenation is described. Easily accessible monoallylated/propargylated substrates were activated either as inexpensive ethyl oxalates or as recyclable 3,5-bis(trifluoromethyl)benzoates to generate alkyl radicals suitable...

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Rackl D, Kais V, Lutsker E, et al. Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. European J Org Chem. 2017;2017(15):2130-2138doi: 10.1002/ejoc.201700014.
Rackl, D., Kais, V., Lutsker, E., & Reiser, A. O. (2017). Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. European journal of organic chemistry, 2017(15), 2130-2138. https://doi.org/10.1002/ejoc.201700014
Rackl, Daniel, et al. "Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation." European journal of organic chemistry vol. 2017,15 (2017): 2130-2138. doi: https://doi.org/10.1002/ejoc.201700014
Rackl D, Kais V, Lutsker E, Reiser AO. Synthesis of Chiral Tetrahydrofurans and Pyrrolidines by Visible-Light-Mediated Deoxygenation. European J Org Chem. 2017 Apr 18;2017(15):2130-2138. doi: 10.1002/ejoc.201700014. Epub 2017 Feb 28. PMID: 28529446; PMCID: PMC5412674.
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Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates.

Angewandte Chemie (International ed. in English)

Feierfeil J, Grossmann A, Magauer T.
PMID: 26255867
Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11835-8. doi: 10.1002/anie.201506232. Epub 2015 Aug 07.

Described is the development of a highly efficient 2π disrotatory ring-opening aromatization sequence using bicyclo[3.1.0]hexan-2-ones. This unprecedented transformation efficiently proceeds under thermal conditions and allows facile construction of uniquely substituted and polyfunctionalized benzoates. In the presence of either amines...

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Feierfeil J, Grossmann A, Magauer T. Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates. Angew Chem Int Ed Engl. 2015;54(40):11835-8doi: 10.1002/anie.201506232.
Feierfeil, J., Grossmann, A., & Magauer, T. (2015). Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates. Angewandte Chemie (International ed. in English), 54(40), 11835-8. https://doi.org/10.1002/anie.201506232
Feierfeil, Johannes, et al. "Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates." Angewandte Chemie (International ed. in English) vol. 54,40 (2015): 11835-8. doi: https://doi.org/10.1002/anie.201506232
Feierfeil J, Grossmann A, Magauer T. Ring Opening of Bicyclo[3.1.0]hexan-2-ones: A Versatile Synthetic Platform for the Construction of Substituted Benzoates. Angew Chem Int Ed Engl. 2015 Sep 28;54(40):11835-8. doi: 10.1002/anie.201506232. Epub 2015 Aug 07. PMID: 26255867.
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Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates.

The Journal of organic chemistry

Pradhan TR, Mendhekar KL, Mohapatra DK.
PMID: 25941839
J Org Chem. 2015 Jun 05;80(11):5517-31. doi: 10.1021/acs.joc.5b00400. Epub 2015 May 20.

The Au(I)-catalyzed regioselective hydration of γ-acetoxy-α,β-acetylinic ester by the assistance of a neighboring carbonyl group has been developed. Varieties of simple primary, secondary, and tertiary γ-acetoxy-α,β-acetylinic esters, even those bearing sensitive functional group in the remote reaction sites, are...

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Pradhan TR, Mendhekar KL, Mohapatra DK. Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates. J Org Chem. 2015;80(11):5517-31doi: 10.1021/acs.joc.5b00400.
Pradhan, T. R., Mendhekar, K. L., & Mohapatra, D. K. (2015). Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates. The Journal of organic chemistry, 80(11), 5517-31. https://doi.org/10.1021/acs.joc.5b00400
Pradhan, Tapas R, et al. "Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates." The Journal of organic chemistry vol. 80,11 (2015): 5517-31. doi: https://doi.org/10.1021/acs.joc.5b00400
Pradhan TR, Mendhekar KL, Mohapatra DK. Synthesis of γ-Acetoxy β-Keto Esters Through Regioselective Hydration of γ-Acetoxy-α,β-alkynoates. J Org Chem. 2015 Jun 05;80(11):5517-31. doi: 10.1021/acs.joc.5b00400. Epub 2015 May 20. PMID: 25941839.
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Ion-neutral complexes formation and 1,3-proton transfer in the chemical ionization of alkylcyclohexyl benzoates.

Chemical communications (Cambridge, England)

Denekamp C, Stanger A.
PMID: 12120382
Chem Commun (Camb). 2002 Feb 07;(3):236-7. doi: 10.1039/b108661h.

CI, CID, labelling experiments and DFT calculations are used for the elucidation of the mechanism for the decomposition of cyclohexyl benzoates, which proceeds through 1,3-H shift and two equilibrating ion-neutral complexes.

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Denekamp C, Stanger A. Ion-neutral complexes formation and 1,3-proton transfer in the chemical ionization of alkylcyclohexyl benzoates. Chem Commun (Camb). 2002;(3):236-7doi: 10.1039/b108661h.
Denekamp, C., & Stanger, A. (2002). Ion-neutral complexes formation and 1,3-proton transfer in the chemical ionization of alkylcyclohexyl benzoates. Chemical communications (Cambridge, England), (3), 236-7. https://doi.org/10.1039/b108661h
Denekamp, Chagit, and Stanger, Amnon. "Ion-neutral complexes formation and 1,3-proton transfer in the chemical ionization of alkylcyclohexyl benzoates." Chemical communications (Cambridge, England) vol. ,3 (2002): 236-7. doi: https://doi.org/10.1039/b108661h
Denekamp C, Stanger A. Ion-neutral complexes formation and 1,3-proton transfer in the chemical ionization of alkylcyclohexyl benzoates. Chem Commun (Camb). 2002 Feb 07;(3):236-7. doi: 10.1039/b108661h. PMID: 12120382.
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Cross-Coupling Reactions of Hypervalent Siloxane Derivatives: An Alternative to Stille and Suzuki Couplings.

The Journal of organic chemistry

Mowery ME, DeShong P.
PMID: 11674236
J Org Chem. 1999 Mar 05;64(5):1684-1688. doi: 10.1021/jo982463h.

Palladium-catalyzed cross-coupling of phenyl, vinyl, and allyl siloxane derivatives proceeded in good to excellent yield with aryl iodides, electron-deficient aryl bromides, and allylic benzoates. Methyl and 2,2,2-trifluoroethyl siloxane derivatives can be employed in the coupling reaction. Electron-donating and -withdrawing...

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Mowery ME, DeShong P. Cross-Coupling Reactions of Hypervalent Siloxane Derivatives: An Alternative to Stille and Suzuki Couplings. J Org Chem. 1999;64(5):1684-1688doi: 10.1021/jo982463h.
Mowery, M. E., & DeShong, P. (1999). Cross-Coupling Reactions of Hypervalent Siloxane Derivatives: An Alternative to Stille and Suzuki Couplings. The Journal of organic chemistry, 64(5), 1684-1688. https://doi.org/10.1021/jo982463h
Mowery, Molly E., and DeShong, Philip. "Cross-Coupling Reactions of Hypervalent Siloxane Derivatives: An Alternative to Stille and Suzuki Couplings." The Journal of organic chemistry vol. 64,5 (1999): 1684-1688. doi: https://doi.org/10.1021/jo982463h
Mowery ME, DeShong P. Cross-Coupling Reactions of Hypervalent Siloxane Derivatives: An Alternative to Stille and Suzuki Couplings. J Org Chem. 1999 Mar 05;64(5):1684-1688. doi: 10.1021/jo982463h. PMID: 11674236.
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Solid-state structures of zinc(II) benzoate complexes. Catalyst precursors for the coupling of carbon dioxide and epoxides.

Inorganic chemistry

Darensbourg DJ, Wildeson JR, Yarbrough JC.
PMID: 11849101
Inorg Chem. 2002 Feb 25;41(4):973-80. doi: 10.1021/ic0107983.

Zinc complexes derived from benzoic acids containing electron-withdrawing substituents have been synthesized from Zn(II)(bis-trimethylsilyl amide)(2) and the corresponding carboxylic acid (2,6-X(2)C(6)H(3)COOH, where X = F, Cl, or OMe) in THF and structurally characterized via X-ray crystallography. The 2,6-difluorobenzoate complex...

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Darensbourg DJ, Wildeson JR, Yarbrough JC. Solid-state structures of zinc(II) benzoate complexes. Catalyst precursors for the coupling of carbon dioxide and epoxides. Inorg Chem. 2002;41(4):973-80doi: 10.1021/ic0107983.
Darensbourg, D. J., Wildeson, J. R., & Yarbrough, J. C. (2002). Solid-state structures of zinc(II) benzoate complexes. Catalyst precursors for the coupling of carbon dioxide and epoxides. Inorganic chemistry, 41(4), 973-80. https://doi.org/10.1021/ic0107983
Darensbourg, Donald J, et al. "Solid-state structures of zinc(II) benzoate complexes. Catalyst precursors for the coupling of carbon dioxide and epoxides." Inorganic chemistry vol. 41,4 (2002): 973-80. doi: https://doi.org/10.1021/ic0107983
Darensbourg DJ, Wildeson JR, Yarbrough JC. Solid-state structures of zinc(II) benzoate complexes. Catalyst precursors for the coupling of carbon dioxide and epoxides. Inorg Chem. 2002 Feb 25;41(4):973-80. doi: 10.1021/ic0107983. PMID: 11849101.
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Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins.

The Journal of organic chemistry

Inoue Y, Wada T, Sugahara N, Yamamoto K, Kimura K, Tong LH, Gao XM, Hou ZJ, Liu Y.
PMID: 11073615
J Org Chem. 2000 Nov 17;65(23):8041-50. doi: 10.1021/jo001262m.

Supramolecular enantiodifferentiating photoisomerization of (Z)-cyclooctene (1Z) to the chiral (E)-isomer (1E) via inclusion and sensitization by modified alpha-, beta-, and/or gamma-cyclodextrin derivatives, possessing benzoate (2a, 3a, 4a), isomeric phthalates (3b-d), and tethered benzamide (3e) chromophores, has been investigated in...

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Inoue Y, Wada T, Sugahara N, et al. Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins. J Org Chem. 2000;65(23):8041-50doi: 10.1021/jo001262m.
Inoue, Y., Wada, T., Sugahara, N., Yamamoto, K., Kimura, K., Tong, L. H., Gao, X. M., Hou, Z. J., & Liu, Y. (2000). Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins. The Journal of organic chemistry, 65(23), 8041-50. https://doi.org/10.1021/jo001262m
Inoue, et al. "Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins." The Journal of organic chemistry vol. 65,23 (2000): 8041-50. doi: https://doi.org/10.1021/jo001262m
Inoue Y, Wada T, Sugahara N, Yamamoto K, Kimura K, Tong LH, Gao XM, Hou ZJ, Liu Y. Supramolecular photochirogenesis. 2. Enantiodifferentiating photoisomerization of cyclooctene included and sensitized by 6-O-modified cyclodextrins. J Org Chem. 2000 Nov 17;65(23):8041-50. doi: 10.1021/jo001262m. PMID: 11073615.
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Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates.

The Journal of organic chemistry

Um IH, Kim KH, Park HR, Fujio M, Tsuno Y.
PMID: 15153028
J Org Chem. 2004 May 28;69(11):3937-42. doi: 10.1021/jo049694a.

Second-order rate constants have been measured for the reactions of 2,4-dinitrophenyl X-substituted benzoates (1a-f) with a series of primary amines in 80 mol % H(2)O/20 mol % DMSO at 25.0 +/- 0.1 degrees C. The Brønsted-type plot for the...

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Um IH, Kim KH, Park HR, et al. Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates. J Org Chem. 2004;69(11):3937-42doi: 10.1021/jo049694a.
Um, I. H., Kim, K. H., Park, H. R., Fujio, M., & Tsuno, Y. (2004). Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates. The Journal of organic chemistry, 69(11), 3937-42. https://doi.org/10.1021/jo049694a
Um, Ik-Hwan, et al. "Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates." The Journal of organic chemistry vol. 69,11 (2004): 3937-42. doi: https://doi.org/10.1021/jo049694a
Um IH, Kim KH, Park HR, Fujio M, Tsuno Y. Effects of amine nature and nonleaving group substituents on rate and mechanism in aminolyses of 2,4-dinitrophenyl X-substituted benzoates. J Org Chem. 2004 May 28;69(11):3937-42. doi: 10.1021/jo049694a. PMID: 15153028.
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