The regioselective nitration of 9,9′-spirobifluorene under mild conditions is reported for the first time by operating under Menke’s and Crivello’s conditions. The optimized protocol allows obtaining 2-nitro and 2,2′-dinitro-9,9′-spirobifluorene in yields of 79 and 95% and, for the first time, 2,2′,7-trinitro-9,9′-spirobifluorene with 66% yield. Besides, the role of dinitrate salt in Crivello’s protocol has been now clarified, which opens novel scenarios in the preparation of functional materials.
Yousif, D., Vaghi, L., Daniliuc, C., Po, R., Papagni, A., Rizzo, F. (2023). Regioselectivity Control in Spirobifluorene Nitration under Mild Conditions: Explaining the Crivello's Reagent Mechanism. JOURNAL OF ORGANIC CHEMISTRY, 88(9), 5285-5290 [10.1021/acs.joc.2c02596].
Regioselectivity Control in Spirobifluorene Nitration under Mild Conditions: Explaining the Crivello's Reagent Mechanism
Yousif, Dawod;Vaghi, Luca;Papagni, Antonio
;
2023
Abstract
The regioselective nitration of 9,9′-spirobifluorene under mild conditions is reported for the first time by operating under Menke’s and Crivello’s conditions. The optimized protocol allows obtaining 2-nitro and 2,2′-dinitro-9,9′-spirobifluorene in yields of 79 and 95% and, for the first time, 2,2′,7-trinitro-9,9′-spirobifluorene with 66% yield. Besides, the role of dinitrate salt in Crivello’s protocol has been now clarified, which opens novel scenarios in the preparation of functional materials.File | Dimensione | Formato | |
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