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Nucleophile-induced transformation of phenoxathiin-based thiacalixarenes
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2021-08-20 , DOI: 10.1039/d1ob01487k
Tomáš Landovský 1 , Martin Babor 2 , Jan Čejka 2 , Václav Eigner 2 , Hana Dvořáková 3 , Martin Krupička 1 , Pavel Lhoták 1
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Oxidized phenoxathiin-based macrocycles, easily accessible thiacalix[4]arene derivatives, consist of a unique set of structural elements representing a key prerequisite for the unexpected reactivity described in this paper. As proposed, the internal strain, imposed by the presence of a heterocyclic moiety, together with a number of electron-withdrawing groups (SO2) opens the way to the cleavage of the macrocyclic skeleton through a cascade of three SNAr reactions triggered by the nucleophilic attack of an SH anion. The whole transformation, which is unparalleled in classical calixarene chemistry, leads to unique linear sulfinic acid derivatives with a rearranged phenoxathiin moiety that can serve as building blocks for macrocyclic systems of a new type.

中文翻译:

亲核试剂诱导的吩氧噻吩基硫杯芳烃转化

基于氧化吩氧噻吩的大环化合物,易于获得的硫杯 [4] 芳烃衍生物,由一组独特的结构元素组成,代表了本文中描述的意外反应性的关键先决条件。正如所提出的,由杂环部分的存在以及许多吸电子基团 (SO 2 )的存在所施加的内部应变为通过三个 S N Ar 反应触发的级联反应打开了大环骨架裂解的途径。 SH -阴离子的亲核攻击。整个转化在经典杯芳烃化学中是无与伦比的,导致独特的线性亚磺酸衍生物具有重排的吩氧噻吩部分,可作为新型大环系统的构建单元。
更新日期:2021-09-02
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