Sequential Tether-Directed Synthesis of Pentakis-Adducts of C-60 with a Mixed [3:2] Octahedral Addition Pattern

Maxouti K, Hirsch A (2018)


Publication Status: Published

Publication Type: Journal article, Original article

Publication year: 2018

Journal

Publisher: WILEY-V C H VERLAG GMBH

Pages Range: 2579-2586

Journal Issue: 20-21

DOI: 10.1002/ejoc.201800091

Abstract

The design of a novel concept for the synthesis of [3:2] pentakis-adducts of fullerene C-60 is presented. A sequential tether-directed, remote functionalization approach is introduced for the construction of the pentakis-adducts. This fullerene derivative embellished with two different addends in two different directions can be considered as a valuable tecton for further functionalization. The stepwise cyclopropanation of C-60 with a macrocyclic tris-malonate and a bis(-keto ester) yielded the corresponding pentakis-adduct with an incomplete octahedral addition pattern. This reaction sequence gave access to two pairs of enantiomers that were easily separated by column chromatography on an achiral stationary phase and subsequently characterized.

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How to cite

APA:

Maxouti, K., & Hirsch, A. (2018). Sequential Tether-Directed Synthesis of Pentakis-Adducts of C-60 with a Mixed [3:2] Octahedral Addition Pattern. European Journal of Organic Chemistry, 20-21, 2579-2586. https://dx.doi.org/10.1002/ejoc.201800091

MLA:

Maxouti, Katerina, and Andreas Hirsch. "Sequential Tether-Directed Synthesis of Pentakis-Adducts of C-60 with a Mixed [3:2] Octahedral Addition Pattern." European Journal of Organic Chemistry 20-21 (2018): 2579-2586.

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