Acta Crystallographica Section C

Crystal Structure Communications

Volume 57, Part 11 (November 2001)

organic compounds

bj1028 scheme

Acta Cryst. (2001). C57, 1313-1315 [ doi:10.1107/S0108270101012951 ]

Diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate and its Diels-Alder adduct with cyclopentadiene

R. A. Toscano, S. Hernández-Ortega, B. Ortiz, R. Sánchez-Obregón, F. Walls and F. Yuste

Abstract: The thermal Diels-Alder cycloadditon reaction of diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate, C₁₆H₁₇NO₅S, with cyclopentadiene gave the pure racemates of two of the four possible diastereomers, with a complete [pi] -facial selectivity and a high (80:20) endo/exo-sulfinyl selectivity. X-ray diffraction studies of diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate and the major isomer of the cycloaddition product, namely diethyl 3-cyano-3-(toluene-4-sulfinyl)bicyclo[2.2.1]hepta-5-ene-2,2-dicarboxylate, C₂₁H₂₃NO₅S, reveal that the conformation of the substituents on the acrylonitrile moiety produces both steric and electronic effects, which affect the stereoselectivity of the reaction.

Formula: C₁₆H₁₇NO₅S and C₂₁H₂₃NO₅S


	Structure factor file (CIF format) (144.3 kbytes) Contains datablock I

	Structure factor file (CIF format) (122.0 kbytes) Contains datablock II

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