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Muthukrishnan S, Sankaranarayanan J, Klima RF, et al. Intramolecular H-atom abstraction in gamma-azido-butyrophenones: formation of 1,5 ketyl iminyl radicals. Org Lett. 2009;11(11):2345-8doi: 10.1021/ol900754a.
Muthukrishnan, S., Sankaranarayanan, J., Klima, R. F., Pace, T. C., Bohne, C., & Gudmundsdottir, A. D. (2009). Intramolecular H-atom abstraction in gamma-azido-butyrophenones: formation of 1,5 ketyl iminyl radicals. Organic letters, 11(11), 2345-8. https://doi.org/10.1021/ol900754a
Muthukrishnan, Sivaramakrishnan, et al. "Intramolecular H-atom abstraction in gamma-azido-butyrophenones: formation of 1,5 ketyl iminyl radicals." Organic letters vol. 11,11 (2009): 2345-8. doi: https://doi.org/10.1021/ol900754a
Muthukrishnan S, Sankaranarayanan J, Klima RF, Pace TC, Bohne C, Gudmundsdottir AD. Intramolecular H-atom abstraction in gamma-azido-butyrophenones: formation of 1,5 ketyl iminyl radicals. Org Lett. 2009 Jun 04;11(11):2345-8. doi: 10.1021/ol900754a. PMID: 19432450.
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Org Lett. 2009 Jun 04;11(11):2345-8. doi: 10.1021/ol900754a.

Intramolecular H-atom abstraction in gamma-azido-butyrophenones: formation of 1,5 ketyl iminyl radicals.

Organic letters

Sivaramakrishnan Muthukrishnan, Jagadis Sankaranarayanan, Rodney F Klima, Tamara C S Pace, Cornelia Bohne, Anna D Gudmundsdottir

Affiliations

  1. Department of Chemistry, University of Cincinnati, PO Box 210172, Cincinnati, Ohio 45221, USA.

PMID: 19432450 DOI: 10.1021/ol900754a

Abstract

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) approximately 300 nm and tau = 15 micros. DFT-TD calculations were used to support the proposed mechanism for formation of the 1,5 ketyl iminyl radicals.

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