Direct Iodination of Isoindolines and Isoindoline Nitroxides as Precursors to Functionalized Nitroxides. Issue 22 (17th June 2013)

• Record Type: Journal Article
• Authors: Fairfull‐Smith, Kathryn E.; Debele, Emmanuel A.; Allen, Jesse P.; Pfrunder, Michael C.; McMurtrie, John C.
• Is Part Of: European journal of organic chemistry. Issue 22(2013)
• Page Start: 4829
• Page End: 4835
• Publication Date: 2013-06-17
• Subjects: Synthetic methods -- Aromatic substitution -- Halogenation -- Radicals -- Nitrogen oxides; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201300313
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract: A new method for the direct aryl iodination of isoindolines and isoindoline nitroxides that utilizes periodic acid and potassium iodide in sulfuric acid is presented. Di‐iodo functionalized tetramethyl and tetraethyl isoindolines and a di‐iodo tetramethyl isoindoline nitroxide were prepared in high yield (70–82 %). The analogous mono‐iodo species were afforded in modest yield (34–48 %). Iodinated nitrones were also obtained from a tetraethyl isoindoline nitroxide. Abstract : A new method that allows direct aryl iodination of isoindolines and isoindoline nitroxides using periodic acid and potassium iodide in sulfuric acid is reported.