Journal
ORGANIC LETTERS
Volume 11, Issue 11, Pages 2345-2348Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol900754a
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Funding
- NSF [CHE-0703920]
- Ohio Supercomputer Center
- Natural Science and Engineering Research Council (NSERC)
- NSERC
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Photolysis of gamma-azidobutyrophenone derivatives yields 1,4 ketyl biradicals via intramolecular H-atom abstraction. The 1,4 ketyl biradicals expel a nitrogen molecule to form 1,5 ketyl iminyl biradicals, which decay by ring closure to form a new carbon-nitrogen bond. The 1,5 ketyl iminyl biradicals were characterized with transient spectroscopy. In argon/nitrogen-saturated solutions, the biradicals have lambda(max) approximate to 300 nm and tau = 15 mu s. DFT-TD calculations were used to support the proposed mechanism for formation of the 1,5 ketyl iminyl radicals.
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