Low energy light-triggered oxidative cleavage of olefins

✍ Scribed by Rajesh S. Murthy; Moses Bio; Youngjae You

• Publisher: Elsevier Science
• Year: 2009
• Tongue: French
• Weight: 237 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.12.069

✦ Synopsis

A series of substituted olefins were tested for their reactivity with singlet oxygen as a singlet oxygenmediated cleavable linker. Low intensity light of 200 mW/cm 2 was irradiated to the solution of an olefin and 5,10,15-triphenyl-20-(4-hydroxyphenyl)-21H,23H-porphyrin under atmospheric condition. Among the tested olefins, 1,2-cis-diphenoxyethylene reacted fast with singlet oxygen, >80% within 15 min yielding a stoichiometric conversion to aldehyde product without any side reactions.