3,5-Bis(ferrocenylmethylene)-1-methyl-4-methylenepiperidine. Synthesis and some chemical properties |
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| Authors: | E I Klimova M Martinez Garcia T Klimova L Ruiz Ramirez J M Mendez Stivalet N N Meleshonkova |
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| Institution: | (1) Facultad de Quimica, Universidad Nacional Autonoma de Mexico, Cd. Universitaria, C.P. 04510 Mexico, D. F., Mexico;(2) Instituto de Quimica, Universidad Nacional Autonoma de Mexico, Cd. Universitaria, C. P. 04510 Mexico, D. F., Mexico;(3) Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, 119899 Moscow, Russian Federation |
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| Abstract: | 3,5-Bis(ferrocenylmethylene)-1-methyl-4-methylenepiperidine, a diferrocenyltriene with a fixeds-cisoid conformation of the exocyclic double bonds, was synthesized. On heating, this compound cyclodimerizes according to
the 4+2]-cycloaddition scheme; it forms Diels-Alder adducts with azodicarboxylic and maleic acidN-phenylimides. The compound easily cyclodimerizes in the presence of acids by a proton cyclodimerization mechanism to give
a spiro cyclodimer. The triene also adds a 3,5-bis(ferrocenylmethylene)-1,4-dimethyl-1-azonia-4-cyclohexyl salt to the terminal
methylene group yielding linear and cyclic addition products.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 511–516, March, 2000. |
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| Keywords: | piperidine triene cyclodimerization dimerization fragmentation allylic cation ferrocene |
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