Abstract
A reaction of tin(IV) bis-o-amidophenolate complex based on redox-active 4,6-di-tert-butyl-N-(2,6-diisopropylphenyl)-o-aminophenol with various allyl halides was studied. This process includes the addition of 1 equiv. of allyl halide to the starting complex and is accompanied by the change in the redox state of one of the redox-active ligands. The reaction results in the formation of a new carbon—carbon bond between the allylic fragment and the carbon atom at position 5 of the ligand o-iminoquinone ring, as well as a tin—halogen bond. The structure and composition of compounds synthesized were confirmed by ESR, NMR, and IR spectroscopy and elemental analysis.
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References
R. Jana, T. P. Pathak, M. S. Sigman, Chem. Rev., 2011, 111, 1417.
I. P. Beletskaya, V. P. Ananikov, Chem. Rev., 2011, 111, 1596.
I. L. Fedushkin, M. V. Moskalev, A. N. Lukoyanov, A. N. Tishkina, E. V. Baranov, G. A. Abakumov, Chem. Eur. J., 2012, 18, 11264.
I. L. Fedushkin, A. S. Nikipelov, K. A. Lyssenko, J. Am. Chem. Soc., 2010, 132, 7874.
A. L. Smith, K. I. Hardcastle, J. D. Soper, J. Am. Chem. Soc., 2010, 132, 14358–14360.
A. L. Smith, L. A. Clapp, K. I. Hardcastle, J. D. Soper, Polyhedron, 2010, 29, 164–169.
A. V. Piskunov, I. N. Meshcheryakova, G. K. Fukin, A. S. Shavyrin, V. K. Cherkasov, G. A. Abakumov, Dalton Trans., 2013, 42, 10533–10539.
J. Emsley, The Elements, Clarendon press, Oxford, 1991, 251 pp.
A. V. Piskunov, I. N. Meshcheryakova, E. V. Baranov, G. K. Fukin, V. K. Cherkasov, G. A. Abakumov, Russ. Chem. Bull. (Int. Ed.), 2010, 59, 361 [Izv. Acad. Nauk, Ser. Khim., 2010, 354].
A. V. Piskunov, I. N. Mescheryakova, G. K. Fukin, E. V. Baranov, M. Hummert, A. S. Shavyrin, V. K. Cherkasov, G. A. Abakumov, Chem. Eur. J., 2008, 14, 10085.
A. J. Gordon, R. A. Ford, The Chemist’s Companion, Wiley interscience publication, New York, 1972. 537 pp.
I. A. Aivaz’yan, A. V. Piskunov, G. K. Fukin, E. V. Baranov, A. S. Shavyrin, V. K. Cherkasov, G. A. Abakumov, Inorg. Chem. Commun., 2006, 9, 612–615.
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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 0912–0915, April, 2014.
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Piskunov, A.V., Piskunova, M.S. & Chegerev, M.G. Formation of a new carbon-carbon bond in the reaction of allyl halides with tin(iv) bis-o-amidophenolate. Russ Chem Bull 63, 912–915 (2014). https://doi.org/10.1007/s11172-014-0527-5
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DOI: https://doi.org/10.1007/s11172-014-0527-5