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Unusual Intramolecular Bridging Reaction in Thiacalix[4]arene Series

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journal contribution
posted on 2009-09-17, 00:00 authored by Ondrej Kundrat, Hana Dvorakova, Ivana Cisarova, Michaela Pojarova, Pavel Lhotak
Thiacalix[4]arene immobilized in the cone conformation undergoes a direct formylation reaction giving unusual products in high yields. The Duff reaction (urotropine/TFA) leads to unprecedented intramolecularly bridged compounds possessing two formyl groups on the opposite para- or para-/meta-positions. The comparison with the corresponding classical calix[4]arene analogues indicates an amazingly different reactivity of the thiacalix[4]arene system.