3-Ferrocenyl-3-(1-naphthyl)cyclopropene. Synthesis, structure, and chemical transformations |
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| Authors: | E I Klimova L Ruiz Ramirez T Klimova Berestneva M Martinez Garcia R Moreno-Esparza C Alvarez Toledano R A Toscano |
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| Institution: | (1) Facultad de Quemica, Universidad Nacional Autonoma de-Mexico, CP 04510 Mexico D. F.;(2) Instituto de Quemica, Universidad Nacional Autonoma de Mexico, CP 04510, Mexico D. F. |
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| Abstract: | Crystalline 3-ferrocenyl-3-(1-naphthyl)cyclopropene was prepared by dehydrobromination ofZ- andE-2-bromo-1-ferrocenyl-1-(1-naphthyl)-cyclopropanes by ButOK in DMSO. The resulting compound and the startingZ-monobromocyclopropane were characterized by X-ray diffraction analysis. The obtained cyclopropene reacts with 1,3-diphenylisobenzofuran
to give a 4+2]-cycloadduct. The small ring opens upon treatment with HBF4 etherate to afford isomericZ- andE-prop-1-enes and 1-ferrocenyl-3H-benzoe]indene. Thermolysis of this cyclopropene results in the formation of 1-ferrocenyl-9bH-benzoe]indene. In all cases, opening of the small ring is accompanied by exclusive alkylation of the naphthalene moiety.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 499–506, March, 1998. |
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| Keywords: | ferrocene cyclopropane and cyclopropene derivatives alkylation dehydrobromination three-membered-ring opening [4+2]-cycloaddition X-ray diffraction analysis |
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