碘控制下由C60与氨基酸酯反应选择性生成吡咯烷基[60]富勒烯和氮丙啶基[60]富勒烯。

Iodo-controlled selective formation of pyrrolidino[60]fullerene and aziridino[60]fullerene from the reaction between C6) and amino acid esters.

作者信息

Zhang Xiang, Gan Liangbing, Huang Shaohua, Shi Yaru

机构信息

Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.

出版信息

J Org Chem. 2004 Aug 20;69(17):5800-2. doi: 10.1021/jo0493368.

DOI:10.1021/jo0493368

PMID:15307764

Abstract

The reaction between glycine methyl ester and C60 can be effectively controlled by different iodo-reagents. Addition of DIB ((diacetoxyiodo)benzene) yields the 2,5-bismethoxycarbonyl pyrrolidino[60]fullerene under ultrasonic irradiation; whereas addition of DIB-iodine results in the N-methoxycarbonylmethyl aziridino[60]fullerene under ultrasonic irradiation. The reaction of sarcosine methyl ester with C60 is similar to that of glycine methyl ester under these two conditions. Addition of just iodine to a mixture of sarcosine methyl ester and C60 affords the tetra(amino)[60]fullerene epoxide C60(O)((Me)NCH2COOMe)4. Possible mechanisms are discussed.

摘要

甘氨酸甲酯与C60之间的反应可通过不同的碘试剂有效控制。添加二乙酰氧基碘苯（DIB）在超声辐射下生成2,5-双甲氧羰基吡咯烷并[60]富勒烯；而添加DIB-碘在超声辐射下则生成N-甲氧羰基甲基氮丙啶并[60]富勒烯。在这两种条件下，肌氨酸甲酯与C60的反应与甘氨酸甲酯的反应相似。仅向肌氨酸甲酯和C60的混合物中添加碘可得到四（氨基）[60]富勒烯环氧化物C60(O)((Me)NCH2COOMe)4。文中讨论了可能的反应机理。