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Sulfur-Incorporating Cyclotriveratrylene Analogues: The Synthesis of Cyclotrithioguaiacylene

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journal contribution
posted on 18.03.2011, 00:00 by Julien Sanseverino, Jean-Claude Chambron, Emmanuel Aubert, Enrique Espinosa
Cyclotriguaiacylene 1 is the universal precursor of cryptophanes, and represents an important intermediate for the preparation of functionalized cavitands of the cyclotriveratrylene family. Its thio analogue (cyclotrithioguaiacylene 3) was synthesized by two different routes, involving either the Newman−Kwart or the Pummerer rearrangement. The latter, performed starting from a trisulfoxide precursor, produced a purer compound in higher overall yield.