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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Autor*in
Xu, Wen-Rong; Chow, Hak-Fun; Cao, Xiao-Ping; Kuck, DietmarUniBi
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.

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.
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PMID: 26126897
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