Photo-Fries Rearrangement of Carbazol-2-yl Sulfonates: Efficient Tool for the Introduction of Sulfonyl Groups into Polycyclic Aromatic Compounds

✍ Scribed by Laura K. Crevatín; Sergio M. Bonesi; Rosa Erra-Balsells

• Publisher: John Wiley and Sons
• Year: 2006
• Tongue: German
• Weight: 105 KB
• Volume: 89
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200690112

✦ Synopsis

Abstract

Systematic studies on the photo‐Fries rearrangement of different 9__H__‐carbazol‐2‐yl sulfonates 2 have shown that this type of conversion can be readily used for the preparative‐scale introduction of alkyl‐ or arylsulfonyl groups into polycyclic aromatic compounds under very mild conditions. A series of new 1‐sulfonyl‐ (3) or 3‐sulfonyl‐9__H__‐carbazoles (4) were prepared in medium‐to‐good yields, and characterized by UV/VIS, ^1^H‐NMR, and ^13^C‐NMR spectroscopy, as well as by elemental analysis. Effects of irradiation wavelength, solvent polarity, presence or absence of O~2~, and photosensitizers were studied in detail.