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Molecules 2017, 22(3), 485; doi:10.3390/molecules22030485

Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling

1
Department of Drug Science and Technology, University of Turin, Via P. Giuria 7, 10125 Turin, Italy
2
Department of Chemistry, University of Turin, Via P. Giuria 7, 10125 Turin, Italy
*
Authors to whom correspondence should be addressed.
Academic Editor: Bernard Martel
Received: 18 November 2016 / Revised: 12 March 2017 / Accepted: 16 March 2017 / Published: 19 March 2017
(This article belongs to the Special Issue Cyclodextrin Chemistry)
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Abstract

A number of influencing factors mean that the random substitution of cyclodextrins (CD) in solution is difficult to reproduce. Reaction assembly in mechanochemistry reduces the number of these factors. However, lack of water can improve the reaction outcomes by minimizing the reagent’s hydrolysis. High-energy ball milling is an efficient, green and simple method for one-step reactions and usually reduces degradation and byproduct formation. Anionic CD derivatives have successfully been synthesized in the solid state, using a planetary ball mill. Comparison with solution reactions, the solvent-free conditions strongly reduced the reagent hydrolysis and resulted in products of higher degree of substitution (DS) with more homogeneous DS distribution. The synthesis of anionic CD derivatives can be effectively performed under mechanochemical activation without significant changes to the substitution pattern but the DS distributions were considerably different from the products of solution syntheses. View Full-Text
Keywords: high-energy ball milling; anionic cyclodextrin; solvent-free reactions; random substitution high-energy ball milling; anionic cyclodextrin; solvent-free reactions; random substitution
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MDPI and ACS Style

Jicsinszky, L.; Caporaso, M.; Calcio Gaudino, E.; Giovannoli, C.; Cravotto, G. Synthesis of Randomly Substituted Anionic Cyclodextrins in Ball Milling. Molecules 2017, 22, 485.

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