Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes

Xu W-R, Chow H-F, Cao X-P, Kuck D (2014)
The Journal of Organic Chemistry 79(19): 9335-9346.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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DOI
Autor*in
Xu, Wen-Rong; Chow, Hak-Fun; Cao, Xiao-Ping; Kuck, DietmarUniBi
Einrichtung
Fakultät für Chemie > Industrielle Organische Chemie und Biotechnologie
Abstract / Bemerkung
The regiocontrolled syntheses of four chiral C-1- or C-3-symmetrical tribenzotriquinacene (TBTQ) derivatives bearing methoxy or hydroxy groups at the peripheral positions [(2,6-(OMe)(2), (+/-)-18 and (+/-)-20; 2,6-(OH)(2), (+/-)-19; and 2,6,10-(OMe)(3), (+/-)-21] by two different synthesis protocols are reported. Compounds (+/-)-19, (+/-)-20, and (+/-)-21 and two (already-known) monosubstituted C1-symmetrical TBTQ analogues [2-OH (+/-)-23 and 2-OMe (+/-)-24] were readily resolved by chiral HPLC, and their absolute configurations were determined by X-ray crystallography and/or circular dichroism (CD) studies. Optical resolution of three closely related TBTQ derivatives [2,6-(OMe)(2), (+/-)-18; 2-OMe, (+/-)-22; and 2-OH, (+/-)-25] containing the same peripheral substituents but other bridgehead residues failed. Enantiopure TBTQ derivatives of this sort are considered promising structural motifs toward the construction of molecular squares and cubes
Erscheinungsjahr
2014
Zeitschriftentitel
The Journal of Organic Chemistry
Band
79
Ausgabe
19
Seite(n)
9335-9346
ISSN
0022-3263
Page URI
https://pub.uni-bielefeld.de/record/2703396

Zitieren

Xu W-R, Chow H-F, Cao X-P, Kuck D. Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry. 2014;79(19):9335-9346.
Xu, W. - R., Chow, H. - F., Cao, X. - P., & Kuck, D. (2014). Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry, 79(19), 9335-9346. doi:10.1021/jo501914y
Xu, Wen-Rong, Chow, Hak-Fun, Cao, Xiao-Ping, and Kuck, Dietmar. 2014. “Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes”. The Journal of Organic Chemistry 79 (19): 9335-9346.
Xu, W. - R., Chow, H. - F., Cao, X. - P., and Kuck, D. (2014). Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry 79, 9335-9346.
Xu, W.-R., et al., 2014. Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry, 79(19), p 9335-9346.
W.-R. Xu, et al., “Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes”, The Journal of Organic Chemistry, vol. 79, 2014, pp. 9335-9346.
Xu, W.-R., Chow, H.-F., Cao, X.-P., Kuck, D.: Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes. The Journal of Organic Chemistry. 79, 9335-9346 (2014).
Xu, Wen-Rong, Chow, Hak-Fun, Cao, Xiao-Ping, and Kuck, Dietmar. “Regiocontrolled Synthesis and Optical Resolution of Mono-, Di-, and Trisubstituted Tribenzotriquinacene Derivatives: Key Building Blocks for Further Assembly into Molecular Squares and Cubes”. The Journal of Organic Chemistry 79.19 (2014): 9335-9346.

8 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Switching the Statistical C3 /C1 Ratio in the Threefold Aromatic Substitution of Tribenzotriquinacenes towards the C3 Isomer.
Wagner P, Rominger F, Mastalerz M., Angew Chem Int Ed Engl 57(35), 2018
PMID: 29938890
Stereoselective synthesis of enantiomerically pure bowl-shaped hydroxytribenzotriquinacenes.
Rommelmann P, Nachtigall B, Guntelmann T, Gröger H, Kuck D., Org Biomol Chem 16(31), 2018
PMID: 30033471
Centrohexaindane: six benzene rings mutually fixed in three dimensions - solid-state structure and six-fold nitration.
Kuck D, Linke J, Teichmann LC, Barth D, Tellenbröker J, Gestmann D, Neumann B, Stammler HG, Bögge H., Phys Chem Chem Phys 18(17), 2016
PMID: 26728545
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Dhara A, Weinmann J, Krause AM, Beuerle F., Chemistry 22(35), 2016
PMID: 27444414
Facile Assembly of Chiral Metallosquares by Using Enantiopure Tribenzotriquinacene Corner Motifs.
Xu WR, Xia GJ, Chow HF, Cao XP, Kuck D., Chemistry 21(34), 2015
PMID: 26126897
Shape-Controlled Synthesis and Self-Sorting of Covalent Organic Cage Compounds.
Klotzbach S, Beuerle F., Angew Chem Int Ed Engl 54(35), 2015
PMID: 26136295
From Fragmentation to Construction--from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three-Dimensional Polycyclic Aromatic Hydrocarbons.
Kuck D., Chem Rec 15(6), 2015
PMID: 26202384
Enantiomerically Pure Tribenzotriquinacenes through Stereoselective Synthesis.
Greschner W, Neumann B, Stammler HG, Gröger H, Kuck D., Angew Chem Int Ed Engl 54(46), 2015
PMID: 26404021

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