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- W2334761560 abstract "The bis-homo Diels–Alder reactions of maleimide and <i>N</i>-methylmaleimide with quadricyclane are shown to produce mixtures containing both the <i>exo</i>,<i>anti</i>- and <i>exo</i>,<i>syn</i>-tricyclo-[4.2.1.0<sup>2,5</sup>]nona-7-ene-3,4-dicarboximides, whereas the isomeric <i>endo</i>,<i>anti</i>-adducts are available from the reaction of cyclopentadiene with the appropriate cyclobutene-3,4-dicarboximides. The related reaction of quadricyclane with maleic anhydride had been erroneously reported to form single adducts; our work shows that two stereoisomers are actually formed and these have been chemically related to the maleimide and <i>N</i>-methylmaleimide adducts. The proton chemical shifts of the adduct formed by reaction of cyclobutene-3,4-dicarboxylic anhydride with cyclopentadiene have also been miss-assigned. Preparation of [3] and [5] polynorbornane scaffolds with terminal succinimides have been effected by coupling the stereoisomeric adducts at the norbornene π-bond by using 2,5-bis(trifluoromethyl)-1,3,4-oxadiazole and bisepoxide. The spacer shapes and dimensions have been determined by molecular modelling." @default.
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- W2334761560 date "2014-05-20" @default.
- W2334761560 modified "2023-09-26" @default.
- W2334761560 title "The Preparation of Stereoisomeric Tricyclo[4.2.1.02,5]nona-7-ene-3,4-dicarboximides and Anhydrides: Literature Corrections and New Products" @default.
- W2334761560 doi "https://doi.org/10.1055/s-0033-1339031" @default.
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