Rearrangement of dypnones to 1,3,5-triarylbenzenes.
Rearrangement of dypnones to 1,3,5-triarylbenzenes is described. The reaction is proposed to involve an aldol-type self-condensation of dypnones, followed by an intramolecular [2 + 2] cycloaddition and a retro-[2 + 2] cycloaddition. The reaction goes smoothly under obviously milder conditions in comparison to the cyclotrimerization of acetophenones to 1,3,5-triarylbenzenes (10 mol % of TsOH, 80 °C versus 130-148 °C). This unexpected rearrangement would provide new possible considerations in dypnone-involved organic synthesis.
†School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, China.
Kai
K
Deng
‡Marine College, Shandong University, Weihai 264209, China.
Qi-Yong
QY
Huai
†School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, China.
Zhi-Lun
ZL
Shen
†School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, China.
Hui-Jing
HJ
Li
†School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, China.
Chen
C
Liu
†School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, China.
Yan-Chao
YC
Wu