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À propos de : Synthesis and Intramolecular Reactions oftrans-Cyclohexyl-1,2-bisacrylate        

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  • Synthesis and Intramolecular Reactions oftrans-Cyclohexyl-1,2-bisacrylate
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  • Photocycloaddition of dimethyl cyclobut-1-ene-1,2-dicarboxylate (1) with cyclohexene (7) afforded twophotoadducts 8 and 9 in 44% and 28% yields, respectively.Spontaneous thermal isomerization of 8 gave (4Z,10Z)-dimethyl cyclodeca-4,10-diene-1,4-dicarboxylate (10), whichsubsequently isomerized to produce trans-1,2-cyclohexanebis-α-acrylic acid dimethyl ester 11. Hydride reduction of thebisacrylate 11 gave the trans-octahydro-1H-inden-2-ols 12aand 15 via a novel, stereoselective, intramolecular reaction.Reaction of the bisacrylate 11 with methyllithium affordedthe bis-tertiary alcohol 16. In contrast, lithium dimethylcuprate reacted with the bisacrylate 11 to give the trans-hexahydro-1H-inden-2-one 17 in high yield via a novel,stereoselective, intramolecular reaction.
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