Approaches to open fullerenes: A 1,2,3,4,5,6-hexaadduct of C60

Shih-Ching Chuang, Fernando R. Clemente, Saeed I. Khan, K. N. Houk, Yves Rubin*

*Corresponding author for this work

Research output: Contribution to journalArticle

34 Scopus citations

Abstract

Complete saturation of a single six-membered ring on fullerene C 60 has been achieved. The critical step in this first synthesis of a fully characterized 1,2,3,4,5,6-hexaadduct consisted of a remarkable double 5-exo-trig addition of alkoxyl radicals promoted by lead tetraacetate. Two possible opening pathways ([2 + 2 + 2] retrocycloadditions) for the newly synthesized compound were explored using quantum mechanical calculations. We found that the oxa bridges in the hexaadduct prevent ring opening through the retro[2 + 2 + 2] mechanism due to the high activation barrier and endothermicity of the reaction.

Original languageEnglish
Pages (from-to)4525-4528
Number of pages4
JournalOrganic Letters
Volume8
Issue number20
DOIs
StatePublished - 28 Sep 2006

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