Aluminum carbenoids in the cyclopropanation of fulvenes

I. R. Ramazanov; A. V. Yaroslavova; N. R. Yaubasarov; U. M. Dzhemilev

doi:10.1007/s11172-018-2096-5

Aluminum carbenoids in the cyclopropanation of fulvenes

作者: Ramazanov I.R.¹, Yaroslavova A.V.¹, Yaubasarov N.R.¹, Dzhemilev U.M.¹
隶属关系:
1. Institute of Petrochemistry and Catalysis of the Russian Academy of Sciences
期: 卷 67, 编号 3 (2018)
页面: 479-484
栏目: Full Articles
URL: https://journals.rcsi.science/1066-5285/article/view/242309
DOI: https://doi.org/10.1007/s11172-018-2096-5
ID: 242309

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详细

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.