Dimethylsulfoxide as a kinetic booster for the chemical generation of singlet oxygen in methanol

✍ Scribed by Marion Collinet-Fressancourt; Nathalie Azaroual; Jean-Marie Aubry; Véronique Nardello-Rataj

• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 375 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.10.022

✦ Synopsis

The kinetic booster effect of dimethylsulfoxide on the chemical generation of singlet oxygen, 1 O 2 , from the disproportionation of hydrogen peroxide catalyzed by molybdate ions in methanol has been evidenced by detection of the IR luminescence of 1 O 2 at 1270 nm and by 95 Mo NMR spectroscopy. DMSO interacts rapidly, through a direct oxygen transfer with the stable tetraperoxomolybdate MoðO 2 Þ 4 2À , leading to DMSO 2 and to the unstable triperoxomolybdate MoðO 2 Þ 3 2À , which releases 1 O 2 . The procedure was applied to accelerate the dark singlet oxygenation of b-citronellol and a-terpinene.