The diene condensation of 1-(1-chlorovinyl)cyclohexene (IV) with trans-3-(chloroformyl)acrylic esters and with methyl trans-3-nitroacrylate goes structurally and sterically selectively with formation of trans-syn adducts with the more electronegative group in the ortho position.
The condensation of methyl trans-3-nitroacrylate with 1-vinylcyclohexene (I) was studied, and the structure and configurations of the isomeric adducts formed were proved.
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Segal', G.M., Rybkina, L.P. & Kucherov, V.F. Stereochemistry of cyclic compounds. Communication 61. Structural and steric orientation in the diene condensations of some vinylcycloalkenes with unsymmetrical trans dienophiles. Russ Chem Bull 13, 1368–1373 (1964). https://doi.org/10.1007/BF00850336