Related Experiment Video
Updated: Oct 17, 2025

Preparation and Characterization of C60/Graphene Hybrid Nanostructures
Published on: May 15, 2018
Water-Mediated Thermal Rearrangement of a Cage-Opened C60 Derivative
Yoshifumi Hashikawa1, Yasujiro Murata1
1Institute for Chemical Research, Kyoto University, Uji, Kyoto, 611-0011, Japan.
Abstract:
The partial zipping of a fullerene orifice was achieved by a water-mediated thermal rearrangement at 150 °C for one day while the orifice size changed from 16- to 14-membered ring with the generation of a fused pentagon. The addition of B(C6 F5 )3 was found to facilitate the reaction likely due to the coordination to carbonyl groups on the orifice. By extending the reaction time, the decarbonylation took place to give another 14-membered-ring orifice where the Michael addition of water occurred under acidic conditions. The computational study suggested that the formation of a carboxylic acid and Fischer-type carbene plays a key role in the C-C bond cleavage/reformation processes during the rearrangement.
Related Concept Videos
[3,3] Sigmatropic Rearrangement of 1,5-Dienes: Cope Rearrangement
Thermal Sigmatropic Reactions: Overview
Sigmatropic shifts are classified based on an order term [i, j ], where i and j indicate the number of atoms across which each end of the σ bond migrates. Below are examples of a [3,3] sigmatropic shift in...
Thermal Electrocyclic Reactions: Stereochemistry
Selection Rules: Thermal Activation
Conjugated systems containing an even number of π-electron pairs undergo a conrotatory ring closure. For example, thermal electrocyclization of (2E,4E)-2,4-hexadiene, a conjugated diene containing two π-electron pairs, gives trans-3,4-dimethylcyclobutene.
[3,3] Sigmatropic Rearrangement of Allyl Vinyl Ethers: Claisen Rearrangement
Chair Conformation of Cyclohexane
The hydrogen atoms linked to carbons are arranged in two different axial and equatorial orientations to achieve this...
Cycloaddition Reactions: MO Requirements for Thermal Activation

