Hydrolysis-Initiated Domino Process on the Rim of Open-Cage C₆₀ Derivatives Including Decarbonylation and Double...

Area of Science:

• Fullerene Chemistry
• Organic Synthesis
• Supramolecular Chemistry

Background:

• Open-cage fullerene derivatives offer unique structural properties for advanced applications.
• Controlled functionalization of fullerene cages is crucial for tailoring their properties.
• Understanding reaction mechanisms is key to developing efficient synthetic routes.

Purpose of the Study:

• To investigate the hydrolysis of a specific open-cage C60 derivative.
• To elucidate the reaction mechanism involved in the functional group removal.
• To explore the potential for further modification of the resulting fullerene structure.

Main Methods:

• Hydrolysis reaction using a mixture of hydrochloric acid (HCl), acetic acid (AcOH), and water (H2O).
• Characterization of the starting material and the product using spectroscopic techniques (details not provided in abstract).
• Chemical derivatization of the product with hydroxylamine.

Main Results:

• Simultaneous removal of two hydroxyl groups, one carbonyl group, and one aniline group from the open-cage C60 derivative in a single step.
• Proposal of a domino reaction mechanism to explain the observed transformation.
• Formation of a new open-cage C60 derivative featuring three carbonyl groups at the orifice rim.
• Successful conversion of one carbonyl group into an oxime group using hydroxylamine.

Conclusions:

• The hydrolysis reaction provides an efficient one-step method for de-functionalizing open-cage C60 derivatives.
• The proposed domino mechanism offers insights into the reactivity of these fullerene structures.
• The resulting functionalized C60 derivative serves as a platform for further chemical modifications, such as oxime formation.