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Reaction of 2-methylnaphthalene with hexachlorocyclopentadiene and structural characterization of a new addition-substitution product

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Abstract

2-Methylnaphthalene undergoes Diels-Alder addition and substitution with hexachlorocyclopentadiene to give two products, 1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-10-methyl-1,4;5,8-dimethanotriphenylene 1 and 1,2,3,4,5,6,7,8,13,13,14,14-dodecachloro-1,4,4a,4b,5,8,8a,12b-octahydro-10-(1′,2′,3′,4′,5′-pentachlorocyclopentadienyl)methyl-1,4;5,8-dimethanotriphenylene 2. The molecular structure of 2 has been characterized by X-ray crystallography: C26H9Cl17, monoclinic, space group P21/c, with a = 15.316(3), b = 13.698(3), c = 16.116(3) Å, β = 96.113(3)°, and Z = 4.

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Authors and Affiliations

  1. Department of Chemistry, The Chinese University of Hong Kong Shatin, New Territories, Hong Kong, P.R. China

    Da-Ming Du, Feng Xue, Henry N. C. Wong & Thomas C. W. Mak

  2. Chemistry Department of Shandong, University, Jinan, P.R. China

    Da-Ming Du

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  1. Da-Ming Du
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  2. Feng Xue
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  3. Henry N. C. Wong
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  4. Thomas C. W. Mak
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Du, DM., Xue, F., Wong, H.N.C. et al. Reaction of 2-methylnaphthalene with hexachlorocyclopentadiene and structural characterization of a new addition-substitution product. Journal of Chemical Crystallography 28, 787–790 (1998). https://doi.org/10.1023/A:1021819518557

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  • DOI: https://doi.org/10.1023/A:1021819518557

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