Related Experiment Video
Updated: Jun 12, 2026

Preparation and Characterization of C60/Graphene Hybrid Nanostructures
Published on: May 15, 2018
Synthesis and reactivity of 2H-pyran moiety in [60]fullerene cage skeleton
Dazhi Yang1, Lijun Shi, Huan Huang
1Beijing National Laboratory for Molecular Sciences, Key Laboratory of Bioorganic Chemistry and Molecular Engineering of the Ministry of Education, College of Chemistry and Molecular Engineering, Peking University, Beijing 100871, China.
Abstract:
The cyclopentadienyl type hexa-adduct C(60)(OOtBu)(6) 1 is readily converted into 2H-pyran containing fullerene derivative C(60)(O)(OOH)(OOtBu)(5) 2 in the presence of NaHCO(3) and hydroquinone. In the process, O-O bond of the tert-butylperoxo group on the central pentagon is cleaved, and the fullerene-bound oxygen radical inserts into a 5,6-junction to form the 2H-pyran moiety. Further reactions of 2 led to open-cage fullerenes with a nine-membered orifice and also both 3,4-dihydro-2H-pyran and 3,6-dihydro-2H-pyran containing fullerene derivatives. Mechanisms are proposed involving intramolecular S(N)2' and aza-Michael addition and ketal formation processes.
More Related Videos
07:14Experimental Approaches for the Synthesis of Low-Valent Metal-Organic Frameworks from Multitopic Phosphine Linkers
Published on: May 12, 2023
09:35Preparation of a Corannulene-functionalized Hexahelicene by Copper(I)-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Related Concept Videos
Five-Membered Heterocyclic Aromatic Compounds: Overview
Cycloaddition Reactions: MO Requirements for Thermal Activation
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Cycloaddition Reactions: MO Requirements for Photochemical Activation
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this staggered...