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

Masahiro Hirama; Kimio Akiyama; Parthasarathi Das; Takashi Mita; Martin J. Lear; Kyo ichiro Iida; Itaru Sato; Fumihiko Yoshimura; Toyonobu Usuki; Shozo Tero-Kubota

doi:10.3987/COM-06-S(O)22

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

Masahiro Hirama, Kimio Akiyama, Parthasarathi Das, Takashi Mita, Martin J. Lear, Kyo ichiro Iida, Itaru Sato, Fumihiko Yoshimura, Toyonobu Usuki, Shozo Tero-Kubota

Division of Organic- and Biomaterials Research

Research output: Contribution to journal › Article › peer-review

11 Citations (Scopus)

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.

Original language	English
Pages (from-to)	83-89
Number of pages	7
Journal	Heterocycles
Volume	69
Issue number	1
DOIs	https://doi.org/10.3987/COM-06-S(O)22
Publication status	Published - 2006 Dec 1

ASJC Scopus subject areas

Analytical Chemistry
Pharmacology
Organic Chemistry

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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.",

author = "Masahiro Hirama and Kimio Akiyama and Parthasarathi Das and Takashi Mita and Lear, {Martin J.} and Iida, {Kyo ichiro} and Itaru Sato and Fumihiko Yoshimura and Toyonobu Usuki and Shozo Tero-Kubota",

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T1 - Direct observation of ESR spectra of bicyclic nine-membered enediynes at ambient temperature

AU - Hirama, Masahiro

AU - Akiyama, Kimio

AU - Das, Parthasarathi

AU - Mita, Takashi

AU - Lear, Martin J.

AU - Iida, Kyo ichiro

AU - Sato, Itaru

AU - Yoshimura, Fumihiko

AU - Usuki, Toyonobu

AU - Tero-Kubota, Shozo

PY - 2006/12/1

Y1 - 2006/12/1

N2 - 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.

AB - 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.

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JO - Heterocycles

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ER -

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

Abstract

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