Spin trapping of 13C-labeled p-benzynes generated by masamune-bergman cyclization of bicyclic nine-membered enediynes

Toyonobu Usuki; Takashi Mita; Martin J. Lear; Parthasarathi Das; Fumihiko Yoshimura; Masayuki Inoue; Masahiro Hirama; Kimio Akiyama; Shozo Tero-Kubota

doi:10.1002/anie.200454133

Spin trapping of ¹³C-labeled p-benzynes generated by masamune-bergman cyclization of bicyclic nine-membered enediynes

Toyonobu Usuki, Takashi Mita, Martin J. Lear, Parthasarathi Das, Fumihiko Yoshimura, Masayuki Inoue, Masahiro Hirama, Kimio Akiyama, Shozo Tero-Kubota

Division of Organic- and Biomaterials Research

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

27 Citations (Scopus)

Abstract

A new spin on things? Spin trapping of ¹³C-labeled bicyclic mimics of natural nine-membered enediynes provided persuasive evidence for the spontaneous thermal generation of biradicals 1 and the differential reactivity of the resulting C3 and C6 radical centers (see scheme; ST spin trap; TBS tert-butyldimethylsilyl).

Original language	English
Pages (from-to)	5249-5253
Number of pages	5
Journal	Angewandte Chemie - International Edition
Volume	43
Issue number	39
DOIs	https://doi.org/10.1002/anie.200454133
Publication status	Published - 2004 Oct 4

Keywords

Cyclization
Enediynes
Isotopic labeling
Radicals
Spin trapping

ASJC Scopus subject areas

Catalysis
Chemistry(all)

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Spin trapping of ¹³C-labeled p-benzynes generated by masamune-bergman cyclization of bicyclic nine-membered enediynes. / Usuki, Toyonobu; Mita, Takashi; Lear, Martin J.; Das, Parthasarathi; Yoshimura, Fumihiko; Inoue, Masayuki; Hirama, Masahiro; Akiyama, Kimio; Tero-Kubota, Shozo.

In: Angewandte Chemie - International Edition, Vol. 43, No. 39, 04.10.2004, p. 5249-5253.

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

Usuki, Toyonobu ; Mita, Takashi ; Lear, Martin J. ; Das, Parthasarathi ; Yoshimura, Fumihiko ; Inoue, Masayuki ; Hirama, Masahiro ; Akiyama, Kimio ; Tero-Kubota, Shozo. / Spin trapping of ¹³C-labeled p-benzynes generated by masamune-bergman cyclization of bicyclic nine-membered enediynes. In: Angewandte Chemie - International Edition. 2004 ; Vol. 43, No. 39. pp. 5249-5253.

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AU - Das, Parthasarathi

AU - Yoshimura, Fumihiko

AU - Inoue, Masayuki

AU - Hirama, Masahiro

AU - Akiyama, Kimio

AU - Tero-Kubota, Shozo

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