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以0.096 mmol叠氮磷酸二苯酯(Diphenylphosphorazidate,DPPA)为催化剂,在极性溶剂和0.48 mmol的三乙胺存在的条件下,0.48 mmol芴-9-羧酸可以发生新颖的脱羧反应。考察了水、有机溶剂以及不同物质的量的DPPA和三乙胺对反应收率的影响。并针对反应结果,提出了可能的反应机理,即:反应中芴-9-羧酸形成的碳负离子可以被结构中的五元环稳定,亲核进攻DPPA形成六元环状过渡态,并发生分子内消除反应,得到脱羧产物。
With 0.096 mmol diphenylphosphorazidate (DPPA) as a catalyst, a novel decarboxylation reaction can take place on 0.48 mmol of fluorene-9-carboxylic acid in the presence of a polar solvent and 0.48 mmol of triethylamine. The effects of DPPA and triethylamine on the yield of the reaction were investigated for water, organic solvents and different amounts of substances. Aiming at the reaction results, a possible reaction mechanism was proposed, in which the carbon anions formed by the fluorene-9-carboxylic acid could be stabilized by the five-membered rings in the structure and nucleophilic attack DPPA to form a six-membered cyclic transition state Elimination of intramolecular reaction, to give decarboxylation products.