Acta Phys. -Chim. Sin. ›› 2008, Vol. 24 ›› Issue (06): 955-960.doi: 10.3866/PKU.WHXB20080606

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Mechanism of Absolute Asymmetric Synthesis and Solid-State CD Spectroscopy of BPOB

XUAN Wei-Min; ZOU Fang; CHEN Lei-Qi; FANG Xue-Ming; LIAN Wei; ZHANG Hui   

  1. State Key Laboratory for Physical Chemistry of Solid Surface, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, Fujian Province, P. R. China
  • Received:2008-01-21 Revised:2008-03-14 Published:2008-06-03
  • Contact: LIAN Wei; ZHANG Hui E-mail:huizhang@xmu.edu.cn;lianwei@xmu.edu.cn

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Abstract: 1,3-bis (3-phenyl-3-oxopropanoyl)benzene (BPOB) was prepared by Claisen condensation of acetophenone and dimethyl isophthalate and characterized by elemental analysis, MS, 1H NMR, UV absorption spectrum, solid-state circular dichroism(CD) spectra, and X-ray single-crystal diffraction. The X-ray crystallographic data indicated that BPOB crystallized in a Sohncke group P212121, UV and 1H NMR showed that the enol tautomer was the most dominant form in solution, and the solid-state CD spectra and repeated recrytallization revealed that the formation of chiral BPOB crystals could be regarded as crystallization-induced asymmetric synthesis.

Key words: 1,3-Bis(3-phenyl-3-oxopropanoyl)benzene, Chrial symmetry breaking, Absolute asymmetric synthesis, Chiral crystal, Solid-state circular dichroismspectroscopy