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- W1984272857 abstract "The reactions of 4,6-dinitrobenzofuroxan (DNBF) and 4,6-dinitrobenzofurazan (DNBZ) with isoprene and 2,3-dimethylbutadiene afford stable diadducts (10a-d), which are shown to result from two consecutive and highly stereoselective normal electron-demand Diels-Alder (NEDDA) condensations. These condensations involve the two nitro-activated double bonds of DNBF and DNBZ as the dienophile contributors. Evidence that the first molecule of diene adds to the C6-C7 rather than the C4-C5 double bond has been obtained through 15 N-labelling of the 4-NO2 group of DNBF and NMR characterization of the corresponding short lived monoadducts (9a-d). An unprecedented finding is that these monoadducts undergo subsequent addition of the second molecule of diene to give not only the stable symmetrical NEDDA-NEDDA diadducts 10a-d but also the unsymmetrical diadducts 11a-d resulting from inverse electron demand Diels- Alder (IEDDA) condensations in which the O4N4C4C5 fragment of 9a-d acts as a heterodiene moiety. Although 11a-d are not thermodynamically stable, undergoing a slow conversion to 10a- d in solution, a pure sample of the isoprene-DNBF NEDDA-IEDDA diadduct 11a could be isolated as a crystalline solid and characterized by X-Ray crystallography." @default.
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- W1984272857 date "2004-01-07" @default.
- W1984272857 modified "2023-10-02" @default.
- W1984272857 title "The multifaceted Diels-Alder reactivity of 4,6-dinitrobenzofuroxan and 4,6-dinitrobenzofurazan toward isoprene and 2,3-dimethylbutadiene" @default.
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- W1984272857 doi "https://doi.org/10.3998/ark.5550190.0005.309" @default.
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