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Paper | Special issue | Vol 79, No. 1, 2009, pp.659-667
Published online, 13th November, 2008
DOI: 10.3987/COM-08-S(D)33
Synthesis and Thermal Stability of 3-Substituted 3-Benzostibepines

Shuji Yasuike, Masaaki Ikoma, Naoki Kakusawa, Takashi Tsuchiya, and Jyoji Kurita*

*Faculty of Pharmaceutical Sciences, Hokuriku University, 3-Ho, Kanagawa machi, Kanazawa 920-1181, Japan


Fully unsaturated 3-benzostibepines having various aryl groups on antimony have been prepared by a ring closure reaction of an appropriate antimony dihalide (ArSbBr2) with (Z,Z)-1,2-bis(2-lithiovinyl)benzene generated by treatment of (Z,Z)-1,2-bis(2-bromovinyl)benzene with t-BuLi. All the stibepines obtained here are thermolabile in solution toward heteroatom extrusion. The half-lives of the stibepines estimated from 1H-NMR spectral analysis revealed that the thermal stabilities of the stibepines bearing a heteroatom moiety (N, O) in the vicinity of the antimony are far less stable than others.