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Binding orientation and reactivity of alkyl α,ω-dibromides in water-soluble cavitands

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Abstract

Host–guest complexation of long chain α,ω-dibromides was evaluated in deep water-soluble cavitands 1 and 2. The bound dibromides (C7–C12) tumble rapidly on the NMR timescale and averaged signals were observed. The complexation allows mono hydrolysis of dibromides in aqueous solution. The arrangement of the products in the host–guest complex was fixed in an unsymmetrical manner that protects the guest from further reaction. Up to 93% yields of the mono-alcohols were obtained. The α,ω-dibromides formed a capsule with cavitand 2 and remained unreactive to hydrolysis.

Graphical abstract: Binding orientation and reactivity of alkyl α,ω-dibromides in water-soluble cavitands

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Publication details

The article was received on 03 May 2019, accepted on 08 May 2019 and first published on 15 May 2019


Article type: Paper
DOI: 10.1039/C9OB01018A
Org. Biomol. Chem., 2019, Advance Article

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    Binding orientation and reactivity of alkyl α,ω-dibromides in water-soluble cavitands

    V. Angamuthu, M. Petroselli, F. Rahman, Y. Yu and J. Rebek, Org. Biomol. Chem., 2019, Advance Article , DOI: 10.1039/C9OB01018A

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