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

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.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