Journal
SYNTHESIS-STUTTGART
Volume 45, Issue 6, Pages 734-742Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0032-1318265
Keywords
(hetera)calixarenes; macrocycles; selenium; 1,3,5-triazines; substituent effects
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Funding
- FWO (Fund for Scientific Research - Flanders)
- KU Leuven
- Ministerie voor Wetenschapsbeleid
- Grants-in-Aid for Scientific Research [11F01760] Funding Source: KAKEN
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Selenium-bridged heteracalixarenes were synthesized by convenient one-pot SNAr reactions starting from variously 2-substituted 4,6-dichloro-1,3,5-triazine building blocks. Reactions of these precursors with sodium hydroselenide afforded the selenacalix[3]triazines as the only macrocyclic products. Yields of the cyclotrimers were significantly increased by optimization of the macrocyclization conditions, the optimum parameters being dependent on the triazine functionalization pattern. X-ray diffraction studies allowed unambiguous identification of the structures and comparison with the solid-state features of analogous heteracalixarenes.
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