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Rearrangement of dypnones to 1,3,5-triarylbenzenes
Kai Deng1, Qi-Yong Huai2, Zhi-Lun Shen1
1†School of Marine Science and Technology, Harbin Institute of Technology, Weihai 264209, China.
Abstract:
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.
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