Synthesis and structure of tris(4-ferrocenylphenyl)boroxine and its utility in cross-coupling reaction |
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Authors: | M V Makarov V P Dyadchenko M Yu Antipin |
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Institution: | (1) Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119992 Moscow, Russian Federation;(2) A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991 Moscow, Russian Federation |
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Abstract: | The reaction of 4-bromophenylferrocene with butyllithium followed by treatment of the organolithium compound with tributyl borate afforded tris(4-ferrocenylphenyl)boroxine (2). X-ray diffraction study of the solvate 2·2C6H6 revealed an intermolecular stacking interaction between the boroxine ring and the Cp rings in the crystal structure. Cross-coupling of compound 2 with 4 -bromo-4-nitro-1,1 -biphenyl produced 4 -ferrocenyl-4-nitro-1,1 :4 ,1 -terphenyl (3). X-ray diffraction study of terphenyl 3 showed that this compound crystallizes in the noncentrosymmetric space group P21. In the crystal, molecules 3 are packed in an antiparallel head-to-tail fashion, which is unfavorable for generation of strong nonlinear optical effects.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2657–2662, December, 2004. |
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Keywords: | triarylboroxine terphenyl 4-bromophenylferrocene cross-coupling X-ray diffraction analysis |
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