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Structure-Binding Effects: Comparative Binding of 2-Anilino-6-naphthalenesulfonate by a Series of Alkyl- and Hydroxyalkyl-Substituted β-Cyclodextrins.

The journal of physical chemistry. B

Favrelle A, Gouhier G, Guillen F, Martin C, Mofaddel N, Petit S, Mundy KM, Pitre SP, Wagner BD.
PMID: 26362021
J Phys Chem B. 2015 Oct 08;119(40):12921-30. doi: 10.1021/acs.jpcb.5b07157. Epub 2015 Sep 24.

Cyclodextrins (CDs) are the most widely used organic hosts for the inclusion of guest molecules. CDs can be readily modified through substitutions of the hydroxyl groups, and these modified CDs can have different host binding properties compared to those...

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Favrelle A, Gouhier G, Guillen F, et al. Structure-Binding Effects: Comparative Binding of 2-Anilino-6-naphthalenesulfonate by a Series of Alkyl- and Hydroxyalkyl-Substituted β-Cyclodextrins. J Phys Chem B. 2015;119(40):12921-30doi: 10.1021/acs.jpcb.5b07157.
Favrelle, A., Gouhier, G., Guillen, F., Martin, C., Mofaddel, N., Petit, S., Mundy, K. M., Pitre, S. P., & Wagner, B. D. (2015). Structure-Binding Effects: Comparative Binding of 2-Anilino-6-naphthalenesulfonate by a Series of Alkyl- and Hydroxyalkyl-Substituted β-Cyclodextrins. The journal of physical chemistry. B, 119(40), 12921-30. https://doi.org/10.1021/acs.jpcb.5b07157
Favrelle, Audrey, et al. "Structure-Binding Effects: Comparative Binding of 2-Anilino-6-naphthalenesulfonate by a Series of Alkyl- and Hydroxyalkyl-Substituted β-Cyclodextrins." The journal of physical chemistry. B vol. 119,40 (2015): 12921-30. doi: https://doi.org/10.1021/acs.jpcb.5b07157
Favrelle A, Gouhier G, Guillen F, Martin C, Mofaddel N, Petit S, Mundy KM, Pitre SP, Wagner BD. Structure-Binding Effects: Comparative Binding of 2-Anilino-6-naphthalenesulfonate by a Series of Alkyl- and Hydroxyalkyl-Substituted β-Cyclodextrins. J Phys Chem B. 2015 Oct 08;119(40):12921-30. doi: 10.1021/acs.jpcb.5b07157. Epub 2015 Sep 24. PMID: 26362021.
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Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur.

Journal of the American Chemical Society

Meng L, Fujikawa T, Kuwayama M, Segawa Y, Itami K.
PMID: 27501373
J Am Chem Soc. 2016 Aug 17;138(32):10351-5. doi: 10.1021/jacs.6b06486. Epub 2016 Aug 08.

A simple yet effective method for the formation of thiophene-fused π-systems is reported. When arylethynyl-substituted polycyclic arenes were heated in DMF in the presence of elemental sulfur, the corresponding thiophene-fused polycyclic arenes were obtained via cleavage of the ortho-C-H...

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Meng L, Fujikawa T, Kuwayama M, et al. Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur. J Am Chem Soc. 2016;138(32):10351-5doi: 10.1021/jacs.6b06486.
Meng, L., Fujikawa, T., Kuwayama, M., Segawa, Y., & Itami, K. (2016). Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur. Journal of the American Chemical Society, 138(32), 10351-5. https://doi.org/10.1021/jacs.6b06486
Meng, Lingkui, et al. "Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur." Journal of the American Chemical Society vol. 138,32 (2016): 10351-5. doi: https://doi.org/10.1021/jacs.6b06486
Meng L, Fujikawa T, Kuwayama M, Segawa Y, Itami K. Thiophene-Fused π-Systems from Diarylacetylenes and Elemental Sulfur. J Am Chem Soc. 2016 Aug 17;138(32):10351-5. doi: 10.1021/jacs.6b06486. Epub 2016 Aug 08. PMID: 27501373.
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Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes.

Organic letters

Wagner F, Harms K, Koert U.
PMID: 26536142
Org Lett. 2015 Nov 20;17(22):5670-3. doi: 10.1021/acs.orglett.5b02952. Epub 2015 Nov 04.

γ-Aryl-β-ketoesters can be prepared in one step from aryl bromides and bis(trimethylsilyl) enol ethers using catalytic amounts of Pd(dba)2/t-Bu3P and stoichiometric amounts of Bu3SnF. The wide range of γ-(hetero)aryl-β-ketoesters that can be obtained illustrate the scope and limitations of...

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Wagner F, Harms K, Koert U. Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes. Org Lett. 2015;17(22):5670-3doi: 10.1021/acs.orglett.5b02952.
Wagner, F., Harms, K., & Koert, U. (2015). Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes. Organic letters, 17(22), 5670-3. https://doi.org/10.1021/acs.orglett.5b02952
Wagner, Frederic, et al. "Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes." Organic letters vol. 17,22 (2015): 5670-3. doi: https://doi.org/10.1021/acs.orglett.5b02952
Wagner F, Harms K, Koert U. Hauser-Heck: Efficient Synthesis of γ-Aryl-β-ketoesters en Route to Substituted Naphthalenes. Org Lett. 2015 Nov 20;17(22):5670-3. doi: 10.1021/acs.orglett.5b02952. Epub 2015 Nov 04. PMID: 26536142.
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Multiple transformations of 2-alkynyl-1,8-bis(dimethylamino)naphthalenes into benzo[g]indoles. Pd/Cu-dependent switching of the electrophilic and nucleophilic sites in acetylenic bond and a puzzle of porcelain catalysis.

The Journal of organic chemistry

Filatova EA, Pozharskii AF, Gulevskaya AV, Ozeryanskii VA.
PMID: 25485741
J Org Chem. 2015 Jan 16;80(2):872-81. doi: 10.1021/jo502363t. Epub 2014 Dec 19.

By means of Sonogashira reaction, a series of 2-alkynyl- and 2,7-dialkynyl derivatives of 1,8-bis(dimethylamino)naphthalene ("proton sponge") have been obtained from the corresponding iodides. It was disclosed that changing the reaction conditions and isolation protocol or conducting the model experiments...

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Filatova EA, Pozharskii AF, Gulevskaya AV, et al. Multiple transformations of 2-alkynyl-1,8-bis(dimethylamino)naphthalenes into benzo[g]indoles. Pd/Cu-dependent switching of the electrophilic and nucleophilic sites in acetylenic bond and a puzzle of porcelain catalysis. J Org Chem. 2014;80(2):872-81doi: 10.1021/jo502363t.
Filatova, E. A., Pozharskii, A. F., Gulevskaya, A. V., & Ozeryanskii, V. A. (2015). Multiple transformations of 2-alkynyl-1,8-bis(dimethylamino)naphthalenes into benzo[g]indoles. Pd/Cu-dependent switching of the electrophilic and nucleophilic sites in acetylenic bond and a puzzle of porcelain catalysis. The Journal of organic chemistry, 80(2), 872-81. https://doi.org/10.1021/jo502363t
Filatova, Ekaterina A, et al. "Multiple transformations of 2-alkynyl-1,8-bis(dimethylamino)naphthalenes into benzo[g]indoles. Pd/Cu-dependent switching of the electrophilic and nucleophilic sites in acetylenic bond and a puzzle of porcelain catalysis." The Journal of organic chemistry vol. 80,2 (2015): 872-81. doi: https://doi.org/10.1021/jo502363t
Filatova EA, Pozharskii AF, Gulevskaya AV, Ozeryanskii VA. Multiple transformations of 2-alkynyl-1,8-bis(dimethylamino)naphthalenes into benzo[g]indoles. Pd/Cu-dependent switching of the electrophilic and nucleophilic sites in acetylenic bond and a puzzle of porcelain catalysis. J Org Chem. 2015 Jan 16;80(2):872-81. doi: 10.1021/jo502363t. Epub 2014 Dec 19. PMID: 25485741.
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Decarboxylative polymerization of 2,6-naphthalenedicarboxylic acid at surfaces.

Journal of the American Chemical Society

Gao HY, Held PA, Knor M, Mück-Lichtenfeld C, Neugebauer J, Studer A, Fuchs H.
PMID: 24937642
J Am Chem Soc. 2014 Jul 09;136(27):9658-63. doi: 10.1021/ja5033875. Epub 2014 Jun 26.

Metal-catalyzed polymerization of 2,6-naphthalenedicarboxylic acid (NDCA) to form poly-2,6-naphthalenes at various surfaces is reported. Polymerizations occur via initial formal dehydrogenation of self-assembled diacids with subsequent decarboxylation to give polymeric bisnaphthyl-Cu species at elevated temperature as intermediate structures (

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Gao HY, Held PA, Knor M, et al. Decarboxylative polymerization of 2,6-naphthalenedicarboxylic acid at surfaces. J Am Chem Soc. 2014;136(27):9658-63doi: 10.1021/ja5033875.
Gao, H. Y., Held, P. A., Knor, M., Mück-Lichtenfeld, C., Neugebauer, J., Studer, A., & Fuchs, H. (2014). Decarboxylative polymerization of 2,6-naphthalenedicarboxylic acid at surfaces. Journal of the American Chemical Society, 136(27), 9658-63. https://doi.org/10.1021/ja5033875
Gao, Hong-Ying, et al. "Decarboxylative polymerization of 2,6-naphthalenedicarboxylic acid at surfaces." Journal of the American Chemical Society vol. 136,27 (2014): 9658-63. doi: https://doi.org/10.1021/ja5033875
Gao HY, Held PA, Knor M, Mück-Lichtenfeld C, Neugebauer J, Studer A, Fuchs H. Decarboxylative polymerization of 2,6-naphthalenedicarboxylic acid at surfaces. J Am Chem Soc. 2014 Jul 09;136(27):9658-63. doi: 10.1021/ja5033875. Epub 2014 Jun 26. PMID: 24937642.
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Supramolecular Recognition Induces Nonsynchronous Change of Dye Fluorescence Properties.

The Journal of organic chemistry

Pereira-Vilar A, Martin-Pastor M, Pessêgo M, García-Río L.
PMID: 27385129
J Org Chem. 2016 Aug 05;81(15):6587-95. doi: 10.1021/acs.joc.6b01230. Epub 2016 Jul 21.

Fluorescence behavior of 8-anilino-1-naphthalenesulfonate (ANS) reflects a blue-shift and fluorescence enhancement on decreasing solvent polarity, with both properties affected in a synchronous way in solvent mixtures where ANS senses a homogeneous solvation shell. ANS complexation by cyclodextrins or bovine...

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Pereira-Vilar A, Martin-Pastor M, Pessêgo M, et al. Supramolecular Recognition Induces Nonsynchronous Change of Dye Fluorescence Properties. J Org Chem. 2016;81(15):6587-95doi: 10.1021/acs.joc.6b01230.
Pereira-Vilar, A., Martin-Pastor, M., Pessêgo, M., & García-Río, L. (2016). Supramolecular Recognition Induces Nonsynchronous Change of Dye Fluorescence Properties. The Journal of organic chemistry, 81(15), 6587-95. https://doi.org/10.1021/acs.joc.6b01230
Pereira-Vilar, Alba, et al. "Supramolecular Recognition Induces Nonsynchronous Change of Dye Fluorescence Properties." The Journal of organic chemistry vol. 81,15 (2016): 6587-95. doi: https://doi.org/10.1021/acs.joc.6b01230
Pereira-Vilar A, Martin-Pastor M, Pessêgo M, García-Río L. Supramolecular Recognition Induces Nonsynchronous Change of Dye Fluorescence Properties. J Org Chem. 2016 Aug 05;81(15):6587-95. doi: 10.1021/acs.joc.6b01230. Epub 2016 Jul 21. PMID: 27385129.
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Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals.

Organic letters

Pati K, Gomes Gdos P, Harris T, Alabugin IV.
PMID: 26886747
Org Lett. 2016 Mar 04;18(5):928-31. doi: 10.1021/acs.orglett.5b03522. Epub 2016 Feb 17.

Selective gold(I)-catalyzed rearrangement of aromatic methoxypropynyl acetals leads to fused catechol ethers (1,2-dialkoxynapthalenes) in excellent yields. Furthermore, this process extends to the analogous heterocyclic and aliphatic substrates. Alkyne activation triggers nucleophilic addition of the acetal oxygen that leads to...

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Pati K, Gomes Gdos P, Harris T, et al. Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals. Org Lett. 2016;18(5):928-31doi: 10.1021/acs.orglett.5b03522.
Pati, K., Gomes, G. d. o. s. . P., Harris, T., & Alabugin, I. V. (2016). Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals. Organic letters, 18(5), 928-31. https://doi.org/10.1021/acs.orglett.5b03522
Pati, Kamalkishore, et al. "Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals." Organic letters vol. 18,5 (2016): 928-31. doi: https://doi.org/10.1021/acs.orglett.5b03522
Pati K, Gomes Gdos P, Harris T, Alabugin IV. Fused Catechol Ethers from Gold(I)-Catalyzed Intramolecular Reaction of Propargyl Ethers with Acetals. Org Lett. 2016 Mar 04;18(5):928-31. doi: 10.1021/acs.orglett.5b03522. Epub 2016 Feb 17. PMID: 26886747.
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Rhodium(i)-catalysed skeletal reorganisation of benzofused spiro[3.3]heptanes via consecutive carbon-carbon bond cleavage.

Organic & biomolecular chemistry

Matsuda T, Yuihara I, Kondo K.
PMID: 27357097
Org Biomol Chem. 2016 Aug 07;14(29):7024-7. doi: 10.1039/c6ob01344a. Epub 2016 Jun 30.

Skeletal reorganisation of benzofused spiro[3.3]heptanes has been achieved using rhodium(i) catalysts. The reaction of benzofused 2-(2-pyridylmethylene)spiro[3.3]heptanes proceeds via sequential C-C bond oxidative addition and β-carbon elimination. On the other hand, benzofused spiro[3.3]heptan-2-ols undergo two consecutive β-carbon elimination processes. In...

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Matsuda T, Yuihara I, Kondo K. Rhodium(i)-catalysed skeletal reorganisation of benzofused spiro[3.3]heptanes via consecutive carbon-carbon bond cleavage. Org Biomol Chem. 2016;14(29):7024-7doi: 10.1039/c6ob01344a.
Matsuda, T., Yuihara, I., & Kondo, K. (2016). Rhodium(i)-catalysed skeletal reorganisation of benzofused spiro[3.3]heptanes via consecutive carbon-carbon bond cleavage. Organic & biomolecular chemistry, 14(29), 7024-7. https://doi.org/10.1039/c6ob01344a
Matsuda, Takanori, et al. "Rhodium(i)-catalysed skeletal reorganisation of benzofused spiro[3.3]heptanes via consecutive carbon-carbon bond cleavage." Organic & biomolecular chemistry vol. 14,29 (2016): 7024-7. doi: https://doi.org/10.1039/c6ob01344a
Matsuda T, Yuihara I, Kondo K. Rhodium(i)-catalysed skeletal reorganisation of benzofused spiro[3.3]heptanes via consecutive carbon-carbon bond cleavage. Org Biomol Chem. 2016 Aug 07;14(29):7024-7. doi: 10.1039/c6ob01344a. Epub 2016 Jun 30. PMID: 27357097.
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Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties.

Chemistry (Weinheim an der Bergstrasse, Germany)

Chen MK, Hsin HJ, Wu TC, Kang BY, Lee YW, Kuo MY, Wu YT.
PMID: 24311153
Chemistry. 2014 Jan 07;20(2):598-608. doi: 10.1002/chem.201303357. Epub 2013 Dec 05.

Highly curved buckybowls 3, 4, and 5 were synthesized from planar precursors, fluoranthenes 8, benzo[k]fluoranthenes 10 and naphtho[1,2-k]-cyclopenta[cd]fluoranthenes 12, respectively, using straightforward palladium-catalyzed cyclization reactions. These fluoranthene-based starting materials were easily prepared from 1,8-bis(arylethynyl)naphthalenes 6. Both buckybowls 3 and...

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Chen MK, Hsin HJ, Wu TC, et al. Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties. Chemistry. 2013;20(2):598-608doi: 10.1002/chem.201303357.
Chen, M. K., Hsin, H. J., Wu, T. C., Kang, B. Y., Lee, Y. W., Kuo, M. Y., & Wu, Y. T. (2014). Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties. Chemistry (Weinheim an der Bergstrasse, Germany), 20(2), 598-608. https://doi.org/10.1002/chem.201303357
Chen, Min-Kuan, et al. "Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties." Chemistry (Weinheim an der Bergstrasse, Germany) vol. 20,2 (2014): 598-608. doi: https://doi.org/10.1002/chem.201303357
Chen MK, Hsin HJ, Wu TC, Kang BY, Lee YW, Kuo MY, Wu YT. Highly curved bowl-shaped fragments of fullerenes: synthesis, structural analysis, and physical properties. Chemistry. 2014 Jan 07;20(2):598-608. doi: 10.1002/chem.201303357. Epub 2013 Dec 05. PMID: 24311153.
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Carbonyl J Derivatives: A New Class of HIV-1 Integrase Inhibitors.

Bioorganic chemistry

Maurer K, Tang AH, Kenyon GL, Leavitt AD.
PMID: 10915552
Bioorg Chem. 2000 Jun;28(3):140-155. doi: 10.1006/bioo.2000.1166.

Integration of a DNA copy of the HIV-1 genome is required for viral replication and pathogenicity, and this highly specific molecular process is mediated by the virus-encoded integrase protein. The requirement for integration, combined with the lack of a...

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Maurer K, Tang AH, Kenyon GL, et al. Carbonyl J Derivatives: A New Class of HIV-1 Integrase Inhibitors. Bioorg Chem. 2000;28(3):140-155doi: 10.1006/bioo.2000.1166.
Maurer, K., Tang, A. H., Kenyon, G. L., & Leavitt, A. D. (2000). Carbonyl J Derivatives: A New Class of HIV-1 Integrase Inhibitors. Bioorganic chemistry, 28(3), 140-155. https://doi.org/10.1006/bioo.2000.1166
Maurer, et al. "Carbonyl J Derivatives: A New Class of HIV-1 Integrase Inhibitors." Bioorganic chemistry vol. 28,3 (2000): 140-155. doi: https://doi.org/10.1006/bioo.2000.1166
Maurer K, Tang AH, Kenyon GL, Leavitt AD. Carbonyl J Derivatives: A New Class of HIV-1 Integrase Inhibitors. Bioorg Chem. 2000 Jun;28(3):140-155. doi: 10.1006/bioo.2000.1166. PMID: 10915552.
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Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes.

Organic letters

Ramakrishna TV, Sharp PR.
PMID: 12633095
Org Lett. 2003 Mar 20;5(6):877-9. doi: 10.1021/ol034040u.

[reaction: see text] Commercially available 1-bromobenzocyclobutene is a potentially useful synthon particularly with the application of organometallic methodology. Here we show that it is readily converted into Cp(2)Zr(benzocyclobutadiene), which couples with alkynes or nitriles giving five-membered zirconacycles. Treatment of...

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Ramakrishna TV, Sharp PR. Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes. Org Lett. 2003;5(6):877-9doi: 10.1021/ol034040u.
Ramakrishna, T. V., & Sharp, P. R. (2003). Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes. Organic letters, 5(6), 877-9. https://doi.org/10.1021/ol034040u
Ramakrishna, T V V, and Sharp, Paul R. "Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes." Organic letters vol. 5,6 (2003): 877-9. doi: https://doi.org/10.1021/ol034040u
Ramakrishna TV, Sharp PR. Naphthalenes, isoquinolines, and a benzazocine from zirconocene-copper-mediated coupling of benzocyclobutadiene with nitriles and alkynes. Org Lett. 2003 Mar 20;5(6):877-9. doi: 10.1021/ol034040u. PMID: 12633095.
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Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes.

The Journal of organic chemistry

Toda F, Tanaka K, Watanabe M, Tamura K, Miyahara I, Nakai T, Hirotsu K.
PMID: 11674408
J Org Chem. 1999 Apr 30;64(9):3102-3105. doi: 10.1021/jo982010c.

The sterically bulky t-Bu-substituted derivatives of 1,1,2,2-tetraphenyl-3,8-dichlorobuta[b]naphthalene (5), trans-1,2-tert-butyl-1,2-diphenyl- (8) and 1,1-di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalene (12), were prepared. X-ray analysis of 8 and 12 at 150 K showed that C-C bonds of 8 and 12 are 1.686 and 1.729 Å, respectively. The...

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Toda F, Tanaka K, Watanabe M, et al. Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes. J Org Chem. 1999;64(9):3102-3105doi: 10.1021/jo982010c.
Toda, F., Tanaka, K., Watanabe, M., Tamura, K., Miyahara, I., Nakai, T., & Hirotsu, K. (1999). Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes. The Journal of organic chemistry, 64(9), 3102-3105. https://doi.org/10.1021/jo982010c
Toda, Fumio, et al. "Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes." The Journal of organic chemistry vol. 64,9 (1999): 3102-3105. doi: https://doi.org/10.1021/jo982010c
Toda F, Tanaka K, Watanabe M, Tamura K, Miyahara I, Nakai T, Hirotsu K. Extremely Long C-C Bond in (-)-trans-1,2-Di-tert-butyl-1,2-diphenyl- and 1,1-Di-tert-butyl-2,2-diphenyl-3,8-dichlorocyclobuta[b]naphthalenes. J Org Chem. 1999 Apr 30;64(9):3102-3105. doi: 10.1021/jo982010c. PMID: 11674408.
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