Chemistry of C84 : Separation of Three Constitutional Isomers and Optical Resolution of D2 -C84 by Using the "Bingel-Retro-Bingel" Strategy

Jeanne Crassous; José Rivera; Nicolette S Fender; Lianhe Shu; Luis Echegoyen; Carlo Thilgen; Andreas Herrmann; François Diederich

doi:10.1002/(SICI)1521-3773(19990601)38:11<1613::AID-ANIE1613>3.0.CO;2-M

Chemistry of C₈₄ : Separation of Three Constitutional Isomers and Optical Resolution of D₂ -C₈₄ by Using the "Bingel-Retro-Bingel" Strategy

Angew Chem Int Ed Engl. 1999 Jun 1;38(11):1613-1617. doi: 10.1002/(SICI)1521-3773(19990601)38:11<1613::AID-ANIE1613>3.0.CO;2-M.

Authors

Jeanne Crassous¹, José Rivera², Nicolette S Fender³, Lianhe Shu³, Luis Echegoyen³, Carlo Thilgen⁴, Andreas Herrmann⁴, François Diederich⁴

Affiliations

¹ Laboratoire de Stéréochimie et Interactions Moléculaires, Ecole Normale Supérieure de Lyon, 46, Allée d'Italie, 69364 Lyon Cédex 07 (France).
² Department of Chemistry, Pontifical Catholic University of Puerto Rico, Ponce, Puerto Rico 00731 (USA).
³ Department of Chemistry, University of Miami, Coral Gables, FL 33124 (USA), Fax: (+1) 305-284-4571.
⁴ Laboratorium für Organische Chemie, ETH-Zentrum, Universitätstrasse 16, CH-8092 Zürich (Switzerland), Fax: (+41) 1-632-1109.

Abstract

The pure enantiomers of D₂ -C₈₄ as well as a third constitutional isomer of this higher fullerene were produced by a retro-Bingel reaction on the first organic derivatives of C₈₄ (see scheme). These derivatives were synthesized by Bingel cyclopropenation of C₈₄ , separated, and unambiguously structurally characterized.

Keywords: Bingel reaction; Circular dichroism; Electrochemistry; Fullerenes.