Facile Synthetic Method and Crystal Structure of 2, 3, 3′, 4′-Biphenyltetracarboxylic Dianhydride

Abstract

Abstract: A facile method for the synthesis of 2,3,3′,4′-biphenyltetracarboxylic dianhydride(a-BPDA) was reported, which comprises the steps of the dehalogenative coupling of dimethyl 4-chlorophthalate(4-DMCP) and dimethyl 3-chlorophthalate(3-DMCP) catalyzed by low-cost (Ph₃P)₂NiCl₂, the hydrolysis of tetra-ester and the dehydration of tetra-acid. In contrast to the conventional methods, this method has the advantage of low cost, convenient manipulation, available condition, high purity and good overall yield. Moreover, the single crystal structure of a-BPDA was analyzed by X-ray diffraction method. The X-ray data suggest that a-BPDA is a rigid, non-coplanar and non-linear structure. It contains three crystallographically independent molecules, in which the dihedral angles of the two linked phenyl rings are 44.75(4)°, 46.37(3)° and 42.32(3)°, respectively. The title molecule is governed by a stronger intermolecular interaction in contrast to van der Waals interaction because of the special positions of anhydride groups.

Key words: 2,3,3′,4′-Biphenyltetracarboxylic dianhydride, Crystal structure, Ni-catalyzation, Dehalogenative coupling

YI Shi-xu, GAO Guo-wei, YANG Mei-jia, CHEN Hua, WU Di-feng, MEN Jian. Facile Synthetic Method and Crystal Structure of 2, 3, 3′, 4′-Biphenyltetracarboxylic Dianhydride[J]. Chemical Research in Chinese Universities, 2012, 28(2): 234-238 .

References

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