ArticleThe Journal of organic chemistry2025
Synthesis of Thiacalix[4]arene Skeleton by the Conjugate Addition of Benzoquinone.
Article in The Journal of organic chemistry, 2025. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- The Synergy of Macrocycles and Heterocycles: A Review of Coordination Behavior, Sensing, and Functional Materials Based on Calixarenes.Molecules (Basel, Switzerland) · 2026Review
- Synthesis and Applications of Sulfur-Containing Macrocycles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Review
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7 authors.
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Abstract
Macrocyclic systems having a thiacalix[4]arene-like structure with four bridging sulfur atoms can be easily constructed using benzoquinone and dithiol-based building blocks. The conjugate addition of benzene-1,3-dithiol with two equivalents of 2,6-dimethylbenzoquinone afforded the corresponding hydroquinone trimer, which, after oxidation to benzoquinone, undergoes a final macrocyclization with another benzene-1,3-dithiol molecule. The whole sequence represents a new strategy for the synthesis of macrocycles based on thiacalix[4]arenes. The conformational behavior of these macrocycles was studied using nuclear magnetic resonance and X-ray analyses, and their basic redox properties were investigated with electrochemical methods.
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