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An Approach to the Synthesis of Functionalized Polycyclic Aromatic Hydrocarbons.

European journal of organic chemistry

Little M, Lan H, Raftery J, Morrison JJ, McDouall JJ, Yeates SG, Quayle P.
PMID: 25045320
European J Org Chem. 2013 Sep;2013(27):6038-6041. doi: 10.1002/ejoc.201300750. Epub 2013 Aug 09.

The application of a new benzannulation reaction for the regiocontrolled synthesis of functionalized chrysenes is reported. The initial benzannulation and the subsequent halogen displacement reactions are both highly regiospecific, which thereby enables the regiocontrolled synthesis of a variety of...

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Little M, Lan H, Raftery J, et al. An Approach to the Synthesis of Functionalized Polycyclic Aromatic Hydrocarbons. European J Org Chem. 2013;2013(27):6038-6041doi: 10.1002/ejoc.201300750.
Little, M., Lan, H., Raftery, J., Morrison, J. J., McDouall, J. J., Yeates, S. G., & Quayle, P. (2013). An Approach to the Synthesis of Functionalized Polycyclic Aromatic Hydrocarbons. European journal of organic chemistry, 2013(27), 6038-6041. https://doi.org/10.1002/ejoc.201300750
Little, Mark, et al. "An Approach to the Synthesis of Functionalized Polycyclic Aromatic Hydrocarbons." European journal of organic chemistry vol. 2013,27 (2013): 6038-6041. doi: https://doi.org/10.1002/ejoc.201300750
Little M, Lan H, Raftery J, Morrison JJ, McDouall JJ, Yeates SG, Quayle P. An Approach to the Synthesis of Functionalized Polycyclic Aromatic Hydrocarbons. European J Org Chem. 2013 Sep;2013(27):6038-6041. doi: 10.1002/ejoc.201300750. Epub 2013 Aug 09. PMID: 25045320; PMCID: PMC4068280.
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Sequential oxidative transformation of tetraarylethylenes to 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an oxidant.

Organic letters

Navale TS, Thakur K, Rathore R.
PMID: 21361296
Org Lett. 2011 Apr 01;13(7):1634-7. doi: 10.1021/ol200069c. Epub 2011 Mar 01.

Tetraarylethylenes can be sequentially transformed into 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using 1 and 2 equiv of DDQ, respectively, in CH(2)Cl(2) containing methanesulfonic acid, in excellent yields. Efficient access to substituted dibenzochrysenes from tetraarylethylenes establishes the versatility of this procedure over...

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Navale TS, Thakur K, Rathore R. Sequential oxidative transformation of tetraarylethylenes to 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an oxidant. Org Lett. 2011;13(7):1634-7doi: 10.1021/ol200069c.
Navale, T. S., Thakur, K., & Rathore, R. (2011). Sequential oxidative transformation of tetraarylethylenes to 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an oxidant. Organic letters, 13(7), 1634-7. https://doi.org/10.1021/ol200069c
Navale, Tushar S, et al. "Sequential oxidative transformation of tetraarylethylenes to 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an oxidant." Organic letters vol. 13,7 (2011): 1634-7. doi: https://doi.org/10.1021/ol200069c
Navale TS, Thakur K, Rathore R. Sequential oxidative transformation of tetraarylethylenes to 9,10-diarylphenanthrenes and dibenzo[g,p]chrysenes using DDQ as an oxidant. Org Lett. 2011 Apr 01;13(7):1634-7. doi: 10.1021/ol200069c. Epub 2011 Mar 01. PMID: 21361296.
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Diindeno[1,2,3,4-defg;1',2',3',4'-mnop]chrysenes: solution-phase synthesis and the bowl-to-bowl inversion barrier.

Chemical communications (Cambridge, England)

Chang HI, Huang HT, Huang CH, Kuo MY, Wu YT.
PMID: 20740246
Chem Commun (Camb). 2010 Oct 14;46(38):7241-3. doi: 10.1039/c0cc01730b. Epub 2010 Aug 26.

Diindeno[1,2,3,4-defg;1',2',3',4'-mnop]chrysenes 2 were straightforwardly prepared in around 20% yield from 9,10-diarylphenanthrenes 3 by palladium-catalyzed intramolecular arylations. The bowl-to-bowl inversion barrier for buckybowl 2-iPr is predicted to be approximately 7 kcal mol(-1) based on density functional theory calculations and this...

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Chang HI, Huang HT, Huang CH, et al. Diindeno[1,2,3,4-defg;1',2',3',4'-mnop]chrysenes: solution-phase synthesis and the bowl-to-bowl inversion barrier. Chem Commun (Camb). 2010;46(38):7241-3doi: 10.1039/c0cc01730b.
Chang, H. I., Huang, H. T., Huang, C. H., Kuo, M. Y., & Wu, Y. T. (2010). Diindeno[1,2,3,4-defg;1',2',3',4'-mnop]chrysenes: solution-phase synthesis and the bowl-to-bowl inversion barrier. Chemical communications (Cambridge, England), 46(38), 7241-3. https://doi.org/10.1039/c0cc01730b
Chang, Hung-Ing, et al. "Diindeno[1,2,3,4-defg;1',2',3',4'-mnop]chrysenes: solution-phase synthesis and the bowl-to-bowl inversion barrier." Chemical communications (Cambridge, England) vol. 46,38 (2010): 7241-3. doi: https://doi.org/10.1039/c0cc01730b
Chang HI, Huang HT, Huang CH, Kuo MY, Wu YT. Diindeno[1,2,3,4-defg;1',2',3',4'-mnop]chrysenes: solution-phase synthesis and the bowl-to-bowl inversion barrier. Chem Commun (Camb). 2010 Oct 14;46(38):7241-3. doi: 10.1039/c0cc01730b. Epub 2010 Aug 26. PMID: 20740246.
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Influence of ligand's directional configuration, chrysenes as model compounds, on the binding activity with aryl hydrocarbon receptor.

Scientific reports

Kim T, Zhen J, Lee J, Bauer R, Lee C, Kwon BO, Chae KH, Hong S, Giesy JP, Chang GS, Khim JS.
PMID: 32796895
Sci Rep. 2020 Aug 14;10(1):13821. doi: 10.1038/s41598-020-70704-9.

Understanding what and how physico-chemical factors of a ligand configure conditions for ligand-receptor binding is a key to accurate assessment of toxic potencies of environmental pollutants. We investigated influences of the dipole-driven orientation and resulting directional configuration of ligands...

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Kim T, Zhen J, Lee J, et al. Influence of ligand's directional configuration, chrysenes as model compounds, on the binding activity with aryl hydrocarbon receptor. Sci Rep. 2020;10(1):13821doi: 10.1038/s41598-020-70704-9.
Kim, T., Zhen, J., Lee, J., Bauer, R., Lee, C., Kwon, B. O., Chae, K. H., Hong, S., Giesy, J. P., Chang, G. S., & Khim, J. S. (2020). Influence of ligand's directional configuration, chrysenes as model compounds, on the binding activity with aryl hydrocarbon receptor. Scientific reports, 10(1), 13821. https://doi.org/10.1038/s41598-020-70704-9
Kim, Taewoo, et al. "Influence of ligand's directional configuration, chrysenes as model compounds, on the binding activity with aryl hydrocarbon receptor." Scientific reports vol. 10,1 (2020): 13821. doi: https://doi.org/10.1038/s41598-020-70704-9
Kim T, Zhen J, Lee J, Bauer R, Lee C, Kwon BO, Chae KH, Hong S, Giesy JP, Chang GS, Khim JS. Influence of ligand's directional configuration, chrysenes as model compounds, on the binding activity with aryl hydrocarbon receptor. Sci Rep. 2020 Aug 14;10(1):13821. doi: 10.1038/s41598-020-70704-9. PMID: 32796895; PMCID: PMC7428016.
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Method for the Synthesis of Dibenzo[g,p]Chrysenes: Domino Friedel-Crafts-Type Cyclization of Difluoroethenes Bearing Two Biaryl Groups.

Organic letters

Suzuki N, Fujita T, Ichikawa J.
PMID: 26418965
Org Lett. 2015 Oct 16;17(20):4984-7. doi: 10.1021/acs.orglett.5b02426. Epub 2015 Sep 29.

Dibenzo[g,p]chrysenes were readily synthesized via the superacid- or TiF4-mediated domino Friedel-Crafts-type cyclization of 1,1-difluoroethenes bearing two biaryl groups, which were easily prepared via the Suzuki-Miyaura coupling of 1,1-difluoro-2,2-diiodoethene or 1-(biphenyl-2-yl)-1-bromo-2,2-difluoroethene. Using this approach, the activation of both vinylic and...

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Suzuki N, Fujita T, Ichikawa J. Method for the Synthesis of Dibenzo[g,p]Chrysenes: Domino Friedel-Crafts-Type Cyclization of Difluoroethenes Bearing Two Biaryl Groups. Org Lett. 2015;17(20):4984-7doi: 10.1021/acs.orglett.5b02426.
Suzuki, N., Fujita, T., & Ichikawa, J. (2015). Method for the Synthesis of Dibenzo[g,p]Chrysenes: Domino Friedel-Crafts-Type Cyclization of Difluoroethenes Bearing Two Biaryl Groups. Organic letters, 17(20), 4984-7. https://doi.org/10.1021/acs.orglett.5b02426
Suzuki, Naoto, et al. "Method for the Synthesis of Dibenzo[g,p]Chrysenes: Domino Friedel-Crafts-Type Cyclization of Difluoroethenes Bearing Two Biaryl Groups." Organic letters vol. 17,20 (2015): 4984-7. doi: https://doi.org/10.1021/acs.orglett.5b02426
Suzuki N, Fujita T, Ichikawa J. Method for the Synthesis of Dibenzo[g,p]Chrysenes: Domino Friedel-Crafts-Type Cyclization of Difluoroethenes Bearing Two Biaryl Groups. Org Lett. 2015 Oct 16;17(20):4984-7. doi: 10.1021/acs.orglett.5b02426. Epub 2015 Sep 29. PMID: 26418965.
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Development and application of an analytical method using gas chromatography/triple quadrupole mass spectrometry for characterizing alkylated chrysenes in crude oil samples.

Rapid communications in mass spectrometry : RCM

John GF, Yin F, Mulabagal V, Hayworth JS, Clement TP.
PMID: 24623700
Rapid Commun Mass Spectrom. 2014 Apr 30;28(8):948-56. doi: 10.1002/rcm.6868.

RATIONALE: Recent advances in analytical techniques have led to the development of gas chromatography/triple quadrupole mass spectrometry methods that allow the identification of target analytes in complex environmental samples. We have employed this technology to develop a method for...

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John GF, Yin F, Mulabagal V, et al. Development and application of an analytical method using gas chromatography/triple quadrupole mass spectrometry for characterizing alkylated chrysenes in crude oil samples. Rapid Commun Mass Spectrom. 2014;28(8):948-56doi: 10.1002/rcm.6868.
John, G. F., Yin, F., Mulabagal, V., Hayworth, J. S., & Clement, T. P. (2014). Development and application of an analytical method using gas chromatography/triple quadrupole mass spectrometry for characterizing alkylated chrysenes in crude oil samples. Rapid communications in mass spectrometry : RCM, 28(8), 948-56. https://doi.org/10.1002/rcm.6868
John, G F, et al. "Development and application of an analytical method using gas chromatography/triple quadrupole mass spectrometry for characterizing alkylated chrysenes in crude oil samples." Rapid communications in mass spectrometry : RCM vol. 28,8 (2014): 948-56. doi: https://doi.org/10.1002/rcm.6868
John GF, Yin F, Mulabagal V, Hayworth JS, Clement TP. Development and application of an analytical method using gas chromatography/triple quadrupole mass spectrometry for characterizing alkylated chrysenes in crude oil samples. Rapid Commun Mass Spectrom. 2014 Apr 30;28(8):948-56. doi: 10.1002/rcm.6868. PMID: 24623700.
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Brønsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via Isochromenylium Intermediate Formed in Situ.

The Journal of organic chemistry

Guo B, Zhou Y, Zhang L, Hua R.
PMID: 26180938
J Org Chem. 2015 Aug 07;80(15):7635-41. doi: 10.1021/acs.joc.5b01219. Epub 2015 Jul 24.

Trifluoromethanesulfonic acid (HOTf) promoted cross-coupling of ortho-[2-(4-methoxylphenyl)-alkynyl]acetophenones with ortho-alkynylbenzaldehydes affording chrysene derivatives has been developed. The present cascade reaction provides a facile one-pot synthesis of multisubstituted chrysenes as well as naked chrysene under mild conditions. The mechanism experimental results...

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Guo B, Zhou Y, Zhang L, et al. Brønsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via Isochromenylium Intermediate Formed in Situ. J Org Chem. 2015;80(15):7635-41doi: 10.1021/acs.joc.5b01219.
Guo, B., Zhou, Y., Zhang, L., & Hua, R. (2015). Brønsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via Isochromenylium Intermediate Formed in Situ. The Journal of organic chemistry, 80(15), 7635-41. https://doi.org/10.1021/acs.joc.5b01219
Guo, Biao, et al. "Brønsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via Isochromenylium Intermediate Formed in Situ." The Journal of organic chemistry vol. 80,15 (2015): 7635-41. doi: https://doi.org/10.1021/acs.joc.5b01219
Guo B, Zhou Y, Zhang L, Hua R. Brønsted Acid-Promoted One-Pot Synthesis of Chrysene Derivatives via Isochromenylium Intermediate Formed in Situ. J Org Chem. 2015 Aug 07;80(15):7635-41. doi: 10.1021/acs.joc.5b01219. Epub 2015 Jul 24. PMID: 26180938.
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Functionalized dibenzo[g,p]chrysenes: variable photophysical and electronic properties and liquid-crystal chemistry.

Organic letters

Chaudhuri R, Hsu MY, Li CW, Wang CI, Chen CJ, Lai CK, Chen LY, Liu SH, Wu CC, Liu RS.
PMID: 18563905
Org Lett. 2008 Jul 17;10(14):3053-6. doi: 10.1021/ol801029x. Epub 2008 Jun 19.

The photophysical and electronic properties of dibenzo[ g, p]chrysenes bearing electron-rich and -deficient substituents vary markedly with these substituents. The chemistry of the first liquid-crystalline dibenzo[ g, p]chrysene is also described.

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Chaudhuri R, Hsu MY, Li CW, et al. Functionalized dibenzo[g,p]chrysenes: variable photophysical and electronic properties and liquid-crystal chemistry. Org Lett. 2008;10(14):3053-6doi: 10.1021/ol801029x.
Chaudhuri, R., Hsu, M. Y., Li, C. W., Wang, C. I., Chen, C. J., Lai, C. K., Chen, L. Y., Liu, S. H., Wu, C. C., & Liu, R. S. (2008). Functionalized dibenzo[g,p]chrysenes: variable photophysical and electronic properties and liquid-crystal chemistry. Organic letters, 10(14), 3053-6. https://doi.org/10.1021/ol801029x
Chaudhuri, Rupsha, et al. "Functionalized dibenzo[g,p]chrysenes: variable photophysical and electronic properties and liquid-crystal chemistry." Organic letters vol. 10,14 (2008): 3053-6. doi: https://doi.org/10.1021/ol801029x
Chaudhuri R, Hsu MY, Li CW, Wang CI, Chen CJ, Lai CK, Chen LY, Liu SH, Wu CC, Liu RS. Functionalized dibenzo[g,p]chrysenes: variable photophysical and electronic properties and liquid-crystal chemistry. Org Lett. 2008 Jul 17;10(14):3053-6. doi: 10.1021/ol801029x. Epub 2008 Jun 19. PMID: 18563905.
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Showing 13 to 20 of 20 entries