Synfacts 2010(5): 0530-0530  
DOI: 10.1055/s-0029-1219691
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart ˙ New York

Stable Triplet TMM Diradical

Contributor(s): Timothy M. Swager
K. Matsumoto*, D. Inokuchi, Y. Hirao, H. Kurata, K. Sato, T. Takui, T. Kubo*
Osaka University and Osaka City University, Japan
Further Information

Publication History

Publication Date:
22 April 2010 (online)

Significance

The trimethylenemethane (TMM) diradical is famous as an odd-alternate hydrocarbon with a non-Kekulé triplet ground state. The TMM parent structure has limited stability and previous stable analogues with aromatic-based radicals place small amounts of the radical densities on the carbons of the base TMM structure. The authors make use of the high stability of pyridinyl radicals to create radicals that are terminally stable under inert atmosphere.