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The Secret by Rhonda Byrne Hardback, Excellent yields of the ketones 2o—v were obtained Scheme 4. Notably, the product yield was not significantly affected by the position or electronic nature of the substituents on the aromatic ring of the alcohols. Encouraged by the facile oxidation of benzyl alcohols, the scope of the reaction was finally extended to the formation of more challenging aliphatic aldehydes. Unfortunately, non-activated aliphatic alcohols did not react efficiently under the reaction conditions, and very low alcohol-to-aldehyde conversions occurred.
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The extension of milling times to 3 h failed to result in improved yields of all tested substrates: 3-phenylpropanol, cyclohexanol and nonanol. Despite several attempts to improve the alcohol-to-aldehyde conversion, by, for instance, milling under an oxygen atmosphere and the use of more reactive co-oxidant catalysts [ 69 ], no significant improvements were observed.
We have developed a TEMPO-based oxidative procedure for the air oxidation of primary and secondary benzyl alcohols to the corresponding aldehydes and ketones under ball milling conditions. A library of common alcohols was efficiently converted into carbonyl compounds with no trace of over-oxidation to the carboxylic acids. Under mechanical activation conditions, the reactions provided better yields and proceeded faster than classical, homogeneous phase TEMPO-based oxidations. Studies are underway to identify more effective TEMPO-based catalysts that are also capable of promoting the oxidation of non-activated alcohols.
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General procedure to prepare carbonyl compounds 2a—v. The jar was sealed and ball-milled for 1 min.
Chemistry of the Carbonyl Group - Programmed Approach to Organic Reaction Method
Then, benzyl alcohol The first milling cycle was followed by a break of 2 min leaving in the meantime the uncovered jar in open air. National Center for Biotechnology Information , U. Beilstein J Org Chem.
Published online Oct 2. Author information Article notes Copyright and License information Disclaimer. Corresponding author. Andrea Porcheddu: ti. Received Jun 1; Accepted Sep This article has been cited by other articles in PMC. Abstract The present work addresses the development of an eco-friendly and cost-efficient protocol for the oxidation of primary and secondary alcohols to the corresponding aldehydes and ketones by mechanical processing under air.
Introduction Aldehydes and ketones constitute some of the most powerful and versatile building blocks that are available for a variety of synthetic transformations [ 1 ]. Open in a separate window. Scheme 1. Scheme 2. Scheme 3. Scheme 4.
Conclusion We have developed a TEMPO-based oxidative procedure for the air oxidation of primary and secondary benzyl alcohols to the corresponding aldehydes and ketones under ball milling conditions. Experimental General procedure to prepare carbonyl compounds 2a—v. Click here to view. Notes This article is part of the Thematic Series "Mechanochemistry". References 1. New York: Wiley; Smith B H. Weinheim: Wiley-VCH; Warren S. Tojo G, Fernandez M.
New York: Springer; Hudlucky M. Oxidations in Organic Chemistry. ACS Monograph Series. J Org Chem. Chem Commun.