Density functional theory investigation of the reaction of isodiiodomethane with acetylene: potential utility of isodiiodomethane for cyclopropenation reactions |
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Authors: | Chen Dong Ming Li Yun-Liang Phillips David Lee |
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Institution: | Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong S. A. R., P. R. China. |
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Abstract: | We present density functional theory calculations for the reactions of CH2I-I and CH2I with acetylene (HC triple bond CH) to form a cyclopropene product. CH2I-I readily reacts with HC triple bond CH to form a cyclopropene product and an I2 leaving group via a rate-determining step barrier of approximately 3.9 kcal/mol (B3LYP/Sadlej-pVTZ). Calculations indicated that the CH2I radical reacts to form an iodopropenyl radical, which can close to a cyclopropene only with difficulty. Our results indicate that CH2I-I may act as an effective carbenoid to produce cyclopropenated products from alkynes. |
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