Synthesis and Identification of a Trimethylenemethane Derivative π-Extended with Three Pyridinyl Radicals

A trimethylenemethane (TMM) derivative 12•, in which the parent TMM is π-extended by the symmetric insertion of three pyridine rings into the C−C bonds of TMM, has been synthesized by the alkali metal reduction of the isolated corresponding dication. Although the frozen-glass X-band cw-ESR spectrum...

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Veröffentlicht in:Organic letters 2010-02, Vol.12 (4), p.836-839
Hauptverfasser: Matsumoto, Kouzou, Inokuchi, Daisuke, Hirao, Yasukazu, Kurata, Hiroyuki, Sato, Kazunobu, Takui, Takeji, Kubo, Takashi
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Sprache:eng
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Zusammenfassung:A trimethylenemethane (TMM) derivative 12•, in which the parent TMM is π-extended by the symmetric insertion of three pyridine rings into the C−C bonds of TMM, has been synthesized by the alkali metal reduction of the isolated corresponding dication. Although the frozen-glass X-band cw-ESR spectrum of 12• gave unresolved fine structures due to the small ZFS parameters, pulsed ESR two-dimensional electron spin transient nutation (2D-ESTN) spectroscopy unambiguously can afford to identify diradical 12• as a triplet species.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol902937k