Title

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

Document Type

Article

Publication Date

9-16-2015

Publication Source

Journal of the American Chemical Society

Volume

137

Issue

36

Inclusive pages

11775-82

DOI

10.1021/jacs.5b07207

Abstract

In this work, we briefly report some attempts to control regioisomeric bisadditions on Sc3N@Ih-C80 and Lu3N@Ih-C80 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 Sc3N@C80 and 2 for Lu3N@C80, 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 Ih-C80 cage has not been reported, we present it here.

Disciplines

Chemistry

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