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

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

M.R.C, M.I, S.S.L and L.E. thank the NSF for generous support of this work under the Grant (CHE-1408865). The Robert A. Welch Foundation is also gratefully acknowledged for an endowed chair to L.E. (Grant AH-0033). S.S. thanks the NSF for RUI CHE Grant 1151668. M.G.-B thanks the Spanish MECD for a Ph.D. fellowship (AP2010-2517), and Spanish MINECO for project CTQ2014-52525-P. S.O. thanks the Spanish MINECO CTQ2014-59212-P, Juan de la Cierva Grant (JCI-2012-14438), and the European Community for CIG project (PCIG14-GA-2013-630978)

© Journal of the American Chemical Society, 2015, vol. 137, núm. 36, p. 11775-11782

American Chemical Society (ACS)

Author: Cerón, Maira R.
Izquierdo, Marta
Garcia Borràs, Marc
Lee, Sarah S.
Osuna Oliveras, Sílvia
Echegoyen, Luis A.
Date: 2015 September 16
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
M.R.C, M.I, S.S.L and L.E. thank the NSF for generous support of this work under the Grant (CHE-1408865). The Robert A. Welch Foundation is also gratefully acknowledged for an endowed chair to L.E. (Grant AH-0033). S.S. thanks the NSF for RUI CHE Grant 1151668. M.G.-B thanks the Spanish MECD for a Ph.D. fellowship (AP2010-2517), and Spanish MINECO for project CTQ2014-52525-P. S.O. thanks the Spanish MINECO CTQ2014-59212-P, Juan de la Cierva Grant (JCI-2012-14438), and the European Community for CIG project (PCIG14-GA-2013-630978)
Format: application/pdf
ISSN: 0002-7863 (versió paper)
1520-5126 (versió electrònica)
Document access: http://hdl.handle.net/10256/13148
Language: eng
Publisher: American Chemical Society (ACS)
Collection: MINECO/PN 2011-2015/CTQ2014-52525-P
MINECO/PE 2015-2017/CTQ2014-59212-P
Reproducció digital del document publicat a: http://dx.doi.org/10.1021/jacs.5b07207
Articles publicats (D-Q)
info:eu-repo/grantAgreement/EC/FP7/630978
Is part of: © Journal of the American Chemical Society, 2015, vol. 137, núm. 36, p. 11775-11782
Rights: Tots els drets reservats
Subject: Fullerenes
Ful·lerens
Reaccions d’addició
Addition reactions
Ciclització (Química)
Ring formation (Chemistry)
Title: Bis-1,3-dipolar Cycloadditions on Endohedral Fullerenes M3N@Ih‑C80 (M = Sc, Lu): Remarkable Endohedral-Cluster Regiochemical Control
Type: info:eu-repo/semantics/article
Repository: DUGiDocs

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