Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization

Wiegmann S, Neumann B, Stammler H-G, Mattay J (2012)
European Journal of Organic Chemistry 2012(21): 3955-3961.

Zeitschriftenaufsatz | Veröffentlicht | Englisch
 
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Abstract / Bemerkung
An inherently chiral cyano-substituted resorcin[4]arene has been prepared by palladium-catalyzed cyanation. Based on this reaction, the four cyano groups were converted into ketones, aldehydes, amides, and amines. The ketone derivative was converted into the corresponding macrocycle with four tertiary alcohol functionalities. Furthermore, demethylation of the methoxy groups to give the phenol groups was carried out in the presence of the keto groups. Single-crystal X-ray analysis was performed with the cyano, ketone, tertiary alcohol, and phenol compounds. Changing the methoxy to a phenoxy group also led to a distinct modification of the molecular assembly in the solid state. A study of the tertiary alcohol derivative thereby revealed a remarkable twist of the C2-symmetrical molecule.
Stichworte
X-ray diffraction; Chirality; Macrocycles; Synthetic methods; Calixarenes
Erscheinungsjahr
2012
Zeitschriftentitel
European Journal of Organic Chemistry
Band
2012
Ausgabe
21
Seite(n)
3955-3961
ISSN
1434-193X
Page URI
https://pub.uni-bielefeld.de/record/2523782

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Wiegmann S, Neumann B, Stammler H-G, Mattay J. Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization. European Journal of Organic Chemistry. 2012;2012(21):3955-3961.
Wiegmann, S., Neumann, B., Stammler, H. - G., & Mattay, J. (2012). Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization. European Journal of Organic Chemistry, 2012(21), 3955-3961. doi:10.1002/ejoc.201200507
Wiegmann, S., Neumann, B., Stammler, H. - G., and Mattay, J. (2012). Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization. European Journal of Organic Chemistry 2012, 3955-3961.
Wiegmann, S., et al., 2012. Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization. European Journal of Organic Chemistry, 2012(21), p 3955-3961.
S. Wiegmann, et al., “Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization”, European Journal of Organic Chemistry, vol. 2012, 2012, pp. 3955-3961.
Wiegmann, S., Neumann, B., Stammler, H.-G., Mattay, J.: Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization. European Journal of Organic Chemistry. 2012, 3955-3961 (2012).
Wiegmann, Sebastian, Neumann, Beate, Stammler, Hans-Georg, and Mattay, Jochen. “Inherently Chiral Cyano-Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization”. European Journal of Organic Chemistry 2012.21 (2012): 3955-3961.
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