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Efficient Synthesis of Polyfunctionalized Benzenes in Water via Persulfate-promoted Benzannulation of α,β-Unsaturated Compounds and Alkynes
Published on: December 16, 2019
Reductive benzylation of C₇₀ imidazoline with a bulky addend
Hui-Lei Hou1, Zong-Jun Li, Ying Wang
1State Key Laboratory of Electroanalytical Chemistry, ‡State Key Laboratory of Rare Earth Resources Utilization, Changchun Institute of Applied Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences , 5625 Renmin Street, Changchun, Jilin 130022, P.R. China.
Abstract:
Reductive benzylation of C70 imidazolines bearing a bulky addend has been carried out under conditions similar to that reported for C60 analogues. However, different from the reaction of C60 analogues, the reaction of C70 imidazolines not only results in adducts with 1,2,3,16-configuration due to the steric effect, but also a considerable amount of dibenzylated and monobenzylated products with 1,2,3,4-configuration, demonstrating a reactivity difference between C60 and C70. Interestingly, the anions of the 1,2,3,16-C70 adduct are rather stable as shown by the electrochemical study, which is in contrast to the anions of 1,2,3,16-C60 counterparts, and can be rationalized by the electronic structure difference between C70 and C60 derivatives.
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