2006/02/28 by Toshiyuki Hamura, Yousuke Ibusuki, Hidehiro Uekusa +2 · 1 citation
Chemistry · #Cyclization and Aryne Chemistry #Synthetic Organic Chemistry Methods #Asymmetric Synthesis and Catalysis
paper · doi:10.1021/ja0602647
openalex publication_date 2006/02/28 · openalex created_date 2025/10/10 · openalex updated_date 2026/08/01
Described herein is a synthesis of highly functionalized tricyclobutabenzenes, a class of molecules of structural and theoretical interest. The preparation is based on the repeated [2 + 2] cycloadditions of benzyne and ketene silyl acetals (KSAs), where two types of regioselectivity enable discrimination of the functionalities on the four-membered rings. By these steps, we were able to prepare poly-oxygenated octamethoxytricyclobutabenzene and its hydrolyzed tetra-oxo derivatives. Structural study on the latter compound showed the interesting properties related to the strained four-membered ring.