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Vol. 26 No. 14 (2014): Vol 26 Issue 14

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Theoretical Studies on Cyclopropanation Reaction of Aluminum Carbenoid (CH3)2AlCH2I with Allylic Alcohol

https://doi.org/10.14233/ajchem.2014.16056
Zhaohui Li
Department of Chemistry and Biochemistry, Jiangxi Medical College, Shangrao 334000, P.R. China
Jinglin Shen
Department of Chemistry and Biochemistry, Jiangxi Medical College, Shangrao 334000, P.R. China
Huiqun Hu
Department of Chemistry and Biochemistry, Jiangxi Medical College, Shangrao 334000, P.R. China
Lizhen He
Department of Chemistry and Biochemistry, Jiangxi Medical College, Shangrao 334000, P.R. China

Corresponding Author(s) : Zhaohui Li

lich502@163.com

Asian Journal of Chemistry, Vol. 26 No. 14 (2014): Vol 26 Issue 14

Abstract

The aluminum carbenoid (CH3)2AlCH2I promoted cyclopropanation reactions with allylic alcohol have been investigated. Two reaction channels have been found i.e., the methylene transfer and carbometalation pathways. On the basis of the energetics of the reactions pathways, the methylene transfer pathway (reaction barrier of 9-10.3 kcal/mol) is favored over the carbometalation pathway (about 30 kcal/mol) in the whole reactions. Our computational results are in good agreement with the experimental results performed by Andre B. Charette.

Keywords

Cyclopropanation Density functional theory Aluminum carbenoid Allylic alcohol
Li, Z., Shen, J., Hu, H., & He, L. (2014). Theoretical Studies on Cyclopropanation Reaction of Aluminum Carbenoid (CH3)2AlCH2I with Allylic Alcohol. Asian Journal of Chemistry, 26(14), 4177–4183. https://doi.org/10.14233/ajchem.2014.16056
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