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Aluminum carbenoids in the cyclopropanation of fulvenes

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Abstract

Aluminum carbenoid Et2AlCH2I reacts with 6-substituted fulvenes to give tricyclopropanes in high yields. Calculations at the B3LYP/6-31G(d) level of theory show that coplanar arrangement of the double bonds facilitates cyclopropanation due to conjugation in the transition state. Aluminum carbenoid Et2AlCH2I was generated by either the reaction of equimolar amounts of Et3Al and CH2I2 in hexane or treatment of Et2AlI with CH2N2 in dichloromethane.

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Correspondence to I. R. Ramazanov.

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Dedicated to Academician of the Russian Academy of Sciences I. P. Beletskaya.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0479—0484, March, 2018.

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Ramazanov, I.R., Yaroslavova, A.V., Yaubasarov, N.R. et al. Aluminum carbenoids in the cyclopropanation of fulvenes. Russ Chem Bull 67, 479–484 (2018). https://doi.org/10.1007/s11172-018-2096-5

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  • DOI: https://doi.org/10.1007/s11172-018-2096-5

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