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

Autor: Edward J. Valente, Mark G. Epstein, Warren J. L. Wood
Rok vydání: 2011
Předmět:
Zdroj: Journal of Chemical Crystallography. 41:1060-1063
ISSN: 1572-8854
1074-1542
DOI: 10.1007/s10870-011-0046-2
Popis: 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) A, b = 19.612(4) A, c = 21.353(3) A, α = 90°, β = 90°, γ = 90°, V = 4484.7 (14) A3, 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) A, b = 16.1088(6) A, c = 10.1644(6) A, α = 90°, β = 107.282(5)°, γ = 90°, V = 2097.25(17) A3, 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. 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.
Databáze: OpenAIRE
Externí odkaz: