Direct observation of ESR spectra of bicyclic nine-membered enediynes at ambient temperature

Hirama, Masahiro and Akiyama, Kimio and Das, Parthasarathi and Mita, Takashi and Lear, Martin J. and Iida, Kyo-ichiro and Sato, Itaru and Yoshimura, Fumihiko and Usuki, Toyonobu and Tero-Kubota, Shozo (2006) Direct observation of ESR spectra of bicyclic nine-membered enediynes at ambient temperature. Heterocycles, 69 (1). pp. 83-89. ISSN 0385-5414

Full content URL: http://dx.doi.org/10.3987/COM-06-S(O)22

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Direct observation of ESR spectra of bicyclic nine-membered enediynes at ambient temperature

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Abstract

The ESR spectra for synthetic bicyclo[7.3.0]epoxydodecadienediynes in solution at room temperature are steady. These spectra originate from the Masamune-Bergman cyclization of bicyclo[7.3.0]epoxydodecadienediynes to p-benzyne biradicals and the equilibrium between the two forms. Comparison of the ESR spectra of the unlabeled and 13C-labeled nine-membered enediynes indicated that the spectra are not directly due to the p-benzyne biradicals but rather to more stable secondary radical intermediates.

Keywords:Natural enediynes, Cycloaromatization, Mechanism
Subjects:F Physical Sciences > F160 Organic Chemistry
Divisions:College of Science > School of Chemistry
ID Code:17120
Deposited On:17 Apr 2015 11:27

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