Chemistry of 2,14-Dithiacalix[4]arene: Alkylation and Conformational Behavior of Peralkylated Products.
J Org Chem
; 84(18): 11572-11580, 2019 09 20.
Article
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| MEDLINE
| ID: mdl-31438675
ABSTRACT
2,14-Dithiacalix[4]arene, prepared on a multigram scale, was alkylated using the reaction conditions well known from the chemistry of classical calixarenes or thiacalixarenes to study the specific conformational preferences and dynamic behavior of the corresponding tetraalkylated derivatives. As proved by the combination of the X-ray crystallography and dynamic NMR techniques, the presence of mixed bridges (-CH2- and -S- groups) within the basic skeleton brings about considerable changes in the mutual ratios of the individual conformers compared to the parent macrocycles. Interestingly, certain conformers, hardly accessible for common calixarenes/thiacalixarenes (e.g., 1,2-alternates) are easily prepared in very good yields in the case of 2,14-dithiacalix[4]arene, which makes this mixed-bridge system attractive as molecular scaffold for supramolecular applications.
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Colección:
01-internacional
Base de datos:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Año:
2019
Tipo del documento:
Article
País de afiliación:
República Checa