Competing reaction pathways from α-halo-α-protioalkyl aryl sulfoxides initiated by organometallic reagents |
| |
| Authors: | Paul R. Blakemore Matthew S. Burge Mark A. Sephton |
| |
| Affiliation: | Department of Chemistry, Oregon State University, Corvallis, OR 97331-4003, USA |
| |
| Abstract: | The reactions of syn-1-haloethyl p-chlorophenyl sulfoxides (halogen = Cl, Br) with main-group organometallic reagents (n-BuMgCl, MeLi, n-BuLi, s-BuLi, and t-BuLi) in THF and PhMe solvents were examined. Product distributions were analyzed to determine the extent of competing sulfoxide ligand exchange, halogen-metal exchange, and deprotonation reaction pathways. A combination of t-BuLi in PhMe was optimal for initiation of sulfoxide ligand exchange from syn-1-chloroethyl p-chlorophenyl sulfoxide. |
| |
| Keywords: | Sulfoxide ligand exchange Carbenoids Halogen-metal exchange |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
