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Regiochemistry of the Cycloaddition of Unsymmetrical Alkenes with an Imino-1,2,4-Dithiazole

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Abstract

Two cycloaddition reactions were conducted with 5-(diphenylamino)-3-phenylimino-3H-1,2,4-dithiazole and the unsymmetrical alkenes, methyl acrylate and acrylonitrile, to produce thiazolidines 6 and 7, respectively. X-ray crystal structures of both compounds were obtained. The crystal of 6 is orthorhombic and space group Pbca with crystallographic parameters: a = 10.7090(14) Å, b = 19.612(4) Å, c = 21.353(3) Å, α = 90°, β = 90°, γ = 90°, V = 4484.7 (14) Å3, Z = 8, Dc = 1.326 Mg/m3, F(000) = 1872. The crystal of 7 is monoclinic and space group P2(1)/c with crystallographic parameters: a = 13.4143(5) Å, b = 16.1088(6) Å, c = 10.1644(6) Å, α = 90°, β = 107.282(5)°, γ = 90°, V = 2097.25(17) Å3, Z = 4, Dc = 1.313 Mg/m3, F(000) = 864. The crystal structures confirmed the thiazolidine structure and the predicted regiochemistry of the cycloaddition based on the electronics of the imino-1,2,4-dithiazole and the alkenes.

Index Abstract

Cycloaddition reactions were conducted between 5-(diphenylamino)-3-phenylimino-3H-1,2,4-dithiazole and methyl acrylate or acrylonitrile producing thiazolidine products in which the predicted regiochemistry was established by single-crystal X-ray diffraction.

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Acknowledgments

M.E. and W.W. acknowledge the Medical Research Foundation of Oregon Seed Grant Program, the M. J. Murdock Charitable Trust College Science Research Program and Research Start-Up Grant, and the University of Portland’s Arthur Butine Faculty Development grants for funding. E.V. acknowledges the National Science Foundation (grant MRI 0618148) for diffraction equipment.

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  1. University of Portland, MSC 163, 5000 N. Willamette Blvd., Portland, OR, 97203, USA

    Mark G. Epstein, Edward J. Valente & Warren J. L. Wood

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  1. Mark G. Epstein
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  2. Edward J. Valente
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  3. Warren J. L. Wood
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Correspondence to Warren J. L. Wood.

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Epstein, M.G., Valente, E.J. & Wood, W.J.L. Regiochemistry of the Cycloaddition of Unsymmetrical Alkenes with an Imino-1,2,4-Dithiazole. J Chem Crystallogr 41, 1060–1063 (2011). https://doi.org/10.1007/s10870-011-0046-2

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  • DOI: https://doi.org/10.1007/s10870-011-0046-2

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