Density Functional Theory Investigation ofthe Reaction of Isodiiodomethane withAcetylene: Potential Utility ofIsodiiodomethane for CyclopropenationReactions
We present density functional theory calculationsfor the reactions of CH2I−I and CH2I with acetylene (HC⋮CH) to form a cyclopropene product. CH2I−I readily reactswith HC⋮CH to form a cyclopropene product and an I2leaving group via a rate-determining step barrier of ∼3.9kcal/mol (B3LYP/Sadlej-pVTZ). Calculations indicated thatthe CH2I radical reacts to form an iodopropenyl radical,which can close to a cyclopropene only with difficulty. Ourresults indicate that CH2I−I may act as an effective carbenoid to produce cyclopropenated products from alkynes.