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Inherently Chiral Cyano‐Substituted Resorcin[4]arene: A Promising Starting Point for Further Functionalization
Author(s) -
Wiegmann Sebastian,
Neumann Beate,
Stammler HansGeorg,
Mattay Jochen
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201200507
Subject(s) - chemistry , cyanation , ketone , alcohol , phenol , palladium , molecule , surface modification , derivative (finance) , organic chemistry , medicinal chemistry , catalysis , financial economics , economics
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 C 2 ‐symmetrical molecule.