Regiochemically Controlled Synthesis of a β-4-β' [70]Fullerene Bis-Adduct

Maira R Cerón; Edison Castro; Venkata S Pavan K Neti; Paul W Dunk; Luis A Echegoyen

doi:10.1021/acs.joc.6b02301

Regiochemically Controlled Synthesis of a β-4-β' [70]Fullerene Bis-Adduct

J Org Chem. 2017 Jan 20;82(2):893-897. doi: 10.1021/acs.joc.6b02301. Epub 2017 Jan 9.

Authors

Maira R Cerón^{1

2}, Edison Castro¹, Venkata S Pavan K Neti¹, Paul W Dunk³, Luis A Echegoyen¹

Affiliations

¹ Department of Chemistry, University of Texas at El Paso , 500 West University Avenue, El Paso, Texas 79968, United States.
² Physical and Life Sciences, Lawrence Livermore National Laboratory , 7000 East Avenue, Livermore, California 94550, United States.
³ National High Magnetic Field Laboratory, Florida State University , 1800 East Paul Dirac Drive, Tallahassee, Florida 32310, United States.

PMID: 28006098
DOI: 10.1021/acs.joc.6b02301

Abstract

A β-4-β' C₇₀ bis-adduct regioisomer and an uncommon mono-adduct β-malonate C₇₀ derivative were synthesized by using a Diels-Alder cycloaddition followed by an addition-elimination of bromo-ethylmalonate and a retro-Diels-Alder cycloaddition reaction. We also report the regioselective synthesis and spectroscopic characterization of C_s-symmetric tris- and C_2v-symmetric tetra-adducts of C₇₀, which are the precursors of the mono- and bis-adduct final products.

Publication types

Research Support, Non-U.S. Gov't