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Molecular rearrangement of photoparthenin by BF3-etherate-acetic acid complex: X-ray crystal structure of a novel product

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Abstract

The structure of a novel compound,Iupac name: bicyclo [2.4.0]-octa-1,3-dimethyl-2,3-pentan-9-methylene-8, 10-butan-diolide, which resulted on treatment of photoparthenin with BF3-etherate acetic acid, has been established uniquely by X-ray crystallography. C15H18O4 is orthorhombic, space group P212121, with the cell dimensionsa=8.444(1),b=9.964(2),c=16.239(2) Å,V=1366.3(2) Å3,Z=4,M r =262.3,D o=1.29,D x=1.28 g cm−3, F(000)=560,T=293K,R=0.065 for 818 observed reflections. δ-lactone ring has a skew-boat, γ-lactone ring has an envelope, and the remaining six-membered ring has a distorted chair conformation. The four-membered ring is nonplanar. There are two intramolecular and one intermolecular short C-H⋯O interactions 2.819, 2.834, and 3.259 Å, respectively, which stabilize the crystal structure.

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Authors and Affiliations

  1. Physical and Structural Chemistry Unit, National Chemical Laboratory, 411008, Pune, India

    V. G. Puranik, T. N. Guru Row & S. S. Tavale

  2. Organic Chemistry Division, National Chemical Laboratory, 411008, Pune, India

    B. A. Nagasampagi, M. M. Kulkarni & S. Kasturi Rangachar

Authors
  1. V. G. Puranik
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  2. T. N. Guru Row
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  3. S. S. Tavale
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  4. B. A. Nagasampagi
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  5. M. M. Kulkarni
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  6. S. Kasturi Rangachar
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N.C.L. Communication No. 4583.

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Puranik, V.G., Guru Row, T.N., Tavale, S.S. et al. Molecular rearrangement of photoparthenin by BF3-etherate-acetic acid complex: X-ray crystal structure of a novel product. Journal of Crystallographic and Spectroscopic Research 20, 157–160 (1990). https://doi.org/10.1007/BF01160968

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  • DOI: https://doi.org/10.1007/BF01160968

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