Nucleophile-induced transformation of phenoxathiin-based thiacalixarenes,Organic & Biomolecular Chemistry

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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 S_NAr 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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