Synthesis and Property Study on Homoaromatic Thiabenzenes

ABSTRACT

Thiabenzenes, as nontraditional heterocycles, exhibit both ylide and aromatic character and pose challenges in synthesis, especially in asymmetric synthesis. Their aromaticity also lacks direct experimental evidence. This article introduces a new strategy for synthesizing homoaromatic thiabenzenes using carbene intermediates, achieving high stability and enantioselectivity. The aromaticity of thiabenzene has been identified as homoaromaticity via theoretical calculations and crystallographic data. Additionally, preliminary explorations have been conducted on the chemical reactivity of thiabenzenes, unveiling their unique chemical behaviors and potential for applications.