Synthesis and Properties of <i>ortho</i>-<i>t</i>-BuSO₂C₆H₄-Substituted Iodonium Ylides

Abstract

Iodonium ylides have recently attracted much attention on account of their synthetic applications. However, only a limited number of reports concerning the properties and reactivity of iodonium ylides exist, which is partly due to their instability. In this study, we synthesized several iodonium ylides that bear both an electron-withdrawing group and an aromatic ring with an ortho-t-BuSO2 group. Based on the crystal structures of the synthesized iodonium ylides in combination with natural-bond-orbital (NBO) calculations, we estimated the strength of the intra- and intermolecular halogen-bonding interactions. In addition, we investigated the reactivity of the iodonium ylides under photoirradiation.

Keywords

• halogen bonding
• hypervalent iodine
• NBO analysis
• photochemistry
• radical reactions