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Direct benzyne-C60 addition does not generate a [5,6] open fulleroid
Tetrahedron ( IF 2.1 ) Pub Date : 2017-12-15 , DOI: 10.1016/j.tet.2017.12.023
Ryo Mizunuma , Teruhiko Tanaka , Yoshihiro Nakamura , Yuki Kamijima , Yoshio Kabe

Recent reports describe the different products resulting from the reaction of C60 with benzyne generated from anthranilic acid derivatives and isoamyl nitrate in the presence and absence of triethylamine. Reinvestigation here via 1H, 13C, HMBC NMR and Mass spectroscopy elucidates that these products are the [6,6] closed C60-fused δ lactones, and not the [5,6] open fulleroids which would result from benzyne addition. Furthermore, theoretical calculations show that the open isomer [5,6] benzyne addition is less stable than the [5,6] closed isomer as an isolable product.



中文翻译:

直接添加苯并C 60不会产生[5,6]开富勒烯

最近的报道描述了在三乙胺存在和不存在下,C 60与邻氨基苯甲酸衍生物和硝酸异戊酯生成的苯炔反应生成的不同产物。此处通过1 H,13 C,HMBC NMR和质谱进行的重新研究表明,这些产物是[6,6]封闭的C 60稠合δ内酯,而不是[5,6]开放的富勒烯,这是由于添加了苯并炔而产生的。此外,理论计算表明,作为可分离产物,开放异构体[5,6]苯并炔的稳定性低于[5,6]封闭异构体。

更新日期:2017-12-15
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