Synthesis 2019; 51(10): 2214-2220
DOI: 10.1055/s-0037-1612249
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Hydroxy-Substituted Thiacrown Ethers via Nucleophilic Ring Opening of Epoxides

Monika Stefaniak
,
University of Łódź, Department of Organic and Applied Chemistry, Tamka 12, 91-403 Łódź, Poland   eMail: jaroslaw.romanski@chemia.uni.lodz.pl
› Institutsangaben
Authors acknowledge financial support from National Science Center in Cracow (Poland) (Preludium 9 Grant No. UMO-2015/17/N/ST5/03028).
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Publikationsverlauf

Received: 05. Dezember 2018

Accepted after revision: 21. Januar 2019

Publikationsdatum:
25. Februar 2019 (online)


Abstract

The title thiacrown ethers were prepared in a one-step procedure to give a series of unique macrocycles possessing two unsubstituted hydroxy groups that can be easily functionalized. In addition, epoxides and macrocycles derived from Cookson’s birdcage diketone, were prepared. The nucleophilic ring opening of epoxides synthesis can be classified in the frame of click chemistry. Surprisingly, some of the prepared allyl substituted polyglycols as well as bis-epoxides, especially sulfur analogues, were prepared for the first time.