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