Enol Cation Radicals in Solution, 9. Synthesis and One-Electron Oxidation Chemistry of Novel, Stable Conjugated Dienols and Yne-Enols

✍ Scribed by Schmittel, Michael ;Langels, Anja

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: English
• Weight: 656 KB
• Volume: 1996
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199619960620

✦ Synopsis

Abstract

For the first time stable enols containing the 1,3‐dien‐2‐ol and the yne‐enol functionalities were synthesized, characterized and investigated by cyclic voltammetry. According to the spectral data and AM1 calculations full conjugation between the enol moiety and the vinyl or alkynyl substituents was attained. One‐electron oxidation of enols E1–5 with tris(1,10‐phenanthroline)iron(III) hexafluorophosphate provided in most cases the novel benzofurans B that were isolated and characterized. The mechanism of the benzofuran formation is discussed.