Photorearrangements in spiro-conjoined cyclohexa-2,5-dien-1-one

TETRAHEDRON

卷:67

Article

Suzuki, Masaya¹  Imai, Kazunori¹  Wakabayashi, Hidetsugu¹  Arita, Atsuko²  Johmoto, Kohei²  Uekusa, Hidehiro²  Kobayashi, Keiji¹ 

[1] Josai Univ, Grad Sch Sci, Dept Chem, Sakado, Saitama 3500295, Japan

[2] Tokyo Inst Technol, Dept Chem & Mat Sci, Meguro Ku, Tokyo 1528551, Japan

关键词: Solid-state photoreaction;    Photorearrangement;    Solvate crystal;    X-ray powder diffraction;    Rietveld refinement;   

DOI  :  10.1016/j.tet.2011.05.032

来源: Elsevier

【 摘 要 】

The unexpected formation of cyclohexa-2,5-dien-1-one (6) spiro-conjoined with a dihydrobenzofuran framework, and the photochemical behavior of this compound in solution as well as in the solid state are described. The photoreaction of 6 in solution affords two rearranged products, one (7) accompanied by the enlargement of the oxygen heterocyclic ring and the other (8) accompanied by cyclopentadienone fragmentation. In the solid state, the former is the sole photoproduct of both solvated and desolvated crystals. The desolvated crystals were obtained as polycrystalline solids by thermal release of solvent molecules, and its structure was elucidated by ab initio determination from X-ray powder diffraction data followed by the Rietveld refinement. (C) 2011 Elsevier Ltd. All rights reserved.

【 授权许可】

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