Bis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih-C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control

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• 作者：Maira R. Cer贸n ; Marta Izquierdo ; Marc Garcia-Borr脿s ; Sarah S. Lee ; Steven Stevenson ; S铆lvia Osuna ; Luis Echegoyen
• 刊名：Journal of the American Chemical Society
• 出版年：2015
• 出版时间：September 16, 2015
• 年：2015
• 卷：137
• 期：36
• 页码：11775-11782
• 全文大小：589K
• ISSN：1520-5126

文摘

In this work, we briefly report some attempts to control regioisomeric bisadditions on Sc<sub>3sub>N@I<sub>hsub>-C<sub>80sub> and Lu<sub>3sub>N@I<sub>hsub>-C<sub>80sub> using the tether-controlled multifunctionalization method. We then describe the use of independent (nontethered) bis-1,3-dipolar cycloaddition reactions and the characterization of 5 new bisadducts, 3 for Sc<sub>3sub>N@C<sub>80sub> and 2 for Lu<sub>3sub>N@C<sub>80sub>, which have never been reported before. Unexpectedly and remarkably, 4 of these compounds exhibit relatively high symmetry and 2 of these bisadducts are the first examples of intrinsically chiral endohedral compounds, due to the addition pattern, not to the presence of chiral centers on the addends. Since an analysis of the statistically possible number of bisadduct isomers on an I<sub>hsub>-C<sub>80sub> cage has not been reported, we present it here.