Display options
Cite
Bogdanova A, Popik VV. Photochemical ring opening of 7-benzoyl- and 7-methoxycarbonyldibenzonorcaradienes. competing 1,2-hydrogen shift and cyclization reactions of 1,3-diradicals. Org Lett. 2001;3(12):1885-8doi: 10.1021/ol015938r.
Bogdanova, A., & Popik, V. V. (2001). Photochemical ring opening of 7-benzoyl- and 7-methoxycarbonyldibenzonorcaradienes. competing 1,2-hydrogen shift and cyclization reactions of 1,3-diradicals. Organic letters, 3(12), 1885-8. https://doi.org/10.1021/ol015938r
Bogdanova, A, and Popik, V V. "Photochemical ring opening of 7-benzoyl- and 7-methoxycarbonyldibenzonorcaradienes. competing 1,2-hydrogen shift and cyclization reactions of 1,3-diradicals." Organic letters vol. 3,12 (2001): 1885-8. doi: https://doi.org/10.1021/ol015938r
Bogdanova A, Popik VV. Photochemical ring opening of 7-benzoyl- and 7-methoxycarbonyldibenzonorcaradienes. competing 1,2-hydrogen shift and cyclization reactions of 1,3-diradicals. Org Lett. 2001 Jun 14;3(12):1885-8. doi: 10.1021/ol015938r. PMID: 11405736.
Copy Download .nbib Format: NLM
Share it on

Org Lett. 2001 Jun 14;3(12):1885-8. doi: 10.1021/ol015938r.

Photochemical ring opening of 7-benzoyl- and 7-methoxycarbonyldibenzonorcaradienes. competing 1,2-hydrogen shift and cyclization reactions of 1,3-diradicals.

Organic letters

A Bogdanova, V V Popik

Affiliations

  1. Department of Chemistry, Bowling Green State University, Bowling Green, Ohio 43403, USA.

PMID: 11405736 DOI: 10.1021/ol015938r

Abstract

[see reaction]. The UV irradiation of dibenzonorcaradienes bearing an acyl or alkoxycarbonyl substituent in the 7-position results in formation of substituted phenanthrenes, as well as cis-trans isomerization of the starting material. This reaction apparently proceeds via intermediate formation of a short-lived (tau = 1-20 ns) 1,3-diradical, which is produced by photochemical cleavage of one cyclopropane bond, while no evidence of alpha-carbonylcarbene formation was found.

Publication Types