A Facile Preparation of Alkenyl- and Allenylmetallic Compounds by Means of Iodine-Metal Exchange and Their Use in Organic Synthesis

Article abstract of DOI:10.1016/0040-4020(95)00700-I

Stereospecific lithium-halogen exchange of alkenyl iodides was performed upon treatment with butyllithium in non-polar solvents such as hexane, benzene, and toluene at 25 deg C to provide alkenylllithiums quantitatively with retention of the configuration.Metal-iodine ecxhange of allenyl iodides with n-BuLi, i-PrMgBr or Et2Zn was also performed effectively to afford the corresponding allenylmetallic reagents.An addition of carbonyl compounds to the metallic reagents gave homopropargylic alcohols with high regioselectivity in good yields.