Density functional theory investigation of the reaction of isodiiodomethane with acetylene: potential utility of isodiiodomethane for cyclopropenation reactions.
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.
Chen
Dong Ming
DM
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong S. A. R., P. R. China.
Li
Yun-Liang
YL
Phillips
David Lee
DL