Facile Syntheses of Cavitands with Sulfur-Containing Functional Groups

Abstract

The reactions of the (CH₂Br)₄-cavitand 1 with variable amounts of KSAc produce various (CH₂Br)_4-n(CH₂SAc)_n-cavitands (n = 0-4). Acetyl chloride and the (CH₂SH)₄-cavitand react to generate various (CH₂SH)_4-n(CH₂SAc)_n-cavitands (n = 0-4), which both constitute useful building blocks for hemicarcerand synthesis. Binuclear sulfur-bridged hemicarcerands are available by the reaction of CH₂Br and CH₂SH functional groups in the respective cavitands. The thioacetate protective group in such binuclear cavitands can be cleaved with LiAlH₄ to result in the formation of the respective hemicarcerands with up to six SH groups.

cavitand - thiols - supramolecular chemistry - macrocycles

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