ChemInform Abstract: Photochemistry of ortho-Phenoxymethyl-Substituted Aryl Azides: A Novel Nitrene Rearrangement En Route to Isolable Iminoquinone Methides?

✍ Scribed by Goetz Bucher; Hans-Gert Korth

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 28 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199918052

✦ Synopsis

Photochemistry of ortho-Phenoxymethyl-Substituted Aryl Azides: A Novel Nitrene Rearrangement En Route to Isolable Iminoquinone Methides?

-Investigation of photolysis of azide (I) by means of product analysis and matrix isolation spectroscopy shows that photolysis of azide (I),which is matrix isolated in argon at 10 K, yields a new triplet nitrene (II). Photolysis of (I) in MeCN/diethylamine yields iminoquinone methide (III). A reaction mechanism leading to this surprising product, whose formation necessitates elimination of phenol, via a triplet nitrene (II) is discussed. -(