Aromatic metamorphosis: conversion of an aromatic skeleton into a different ring system.

Area of Science:

• Organic Chemistry
• Synthetic Chemistry
• Catalysis

Background:

• Aromatic skeletons possess high stabilization energy, making them generally resistant to cleavage.
• Endocyclic atom substitution in aromatic cores is less explored than exocyclic functionalization.
• Existing methods often involve complex, multi-step processes for aromatic core modification.

Purpose of the Study:

• To establish a novel strategy termed "aromatic metamorphosis" for transforming aromatic compounds.
• To explore the conversion of common aromatic cores, including dibenzothiophenes, dibenzofurans, and benzofurans, into diverse ring systems.
• To develop efficient, ideally one-step, methods for aromatic ring reconstruction.

Main Methods:

• Utilized a multi-step strategy involving partial disassembly of aromatic cyclic skeletons.
• Employed ring reconstruction techniques to form new chemical structures.
• Investigated conditions for achieving aromatic metamorphosis in a single synthetic step.

Main Results:

• Successfully demonstrated the transformation of dibenzothiophenes, dibenzofurans, and benzofurans into different ring systems.
• Developed a versatile strategy applicable to general aromatic compounds.
• Achieved efficient ring system modification through controlled skeletal rearrangement.

Conclusions:

• "Aromatic metamorphosis" provides a powerful new method for modifying robust aromatic structures.
• This approach opens avenues for synthesizing novel heterocyclic compounds and materials.
• The strategy offers potential for simplified and efficient chemical transformations of aromatic cores.