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Use of Theoretical Chemistry To Explain Baeyer-Villiger Oxidations of Methoxy Aromatic Aldehydes
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Abstract
This is a project for advanced students in two parts.First: A study of the Baeyer-Villiger reaction on para-methoxybenzaldehyde. Such a reaction is commonly used to oxidize ketones into esters. This portion of the study is intended to show advanced students the feasibility of using this reaction on an aromatic aldehyde. The use of monopersuccinic acid (PSA) constitutes an interesting alternative to the classical m-chloroperoxybenzoic acid (mCPBA).Second: The experiment is extended to various polymethoxybenzaldehydes and theoretical calculations are used to explain their particular behaviors. In acid medium at 55 °C the first step of reaction on dimethoxybenzaldehydes is rate determining. This is a special feature, as the rearrangement that constitutes the second step is usually rate determining. Calculations indicate the importance of the dihedral angle between aryl and O-O groups during the rearrangement.
Keywords (Audience):
Upper-Division UndergraduateKeywords (Domain):
Organic ChemistryKeywords (Pedagogy):
Hands-On Learning / ManipulativesKeywords (Subject):
Mechanisms of ReactionsCiting Articles
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This article has been cited by 3 ACS Journal articles (3 most recent appear below).
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Theoretical and Experimental Studies on the Baeyer−Villiger Oxidation of Ketones and the Effect of α-Halo Substituents
Friedrich Grein, Austin C. Chen, David Edwards, and Cathleen M. CruddenThe Journal of Organic Chemistry2006 71 (3), 861-872Theoretical and Experimental Studies on the Baeyer−Villiger Oxidation of Ketones and the Effect of α-Halo Substituents
Friedrich Grein, Austin C. Chen, David Edwards, and Cathleen M. CruddenThe Journal of Organic Chemistry2006 71 (3), 861-872The Baeyer−Villiger reactions of acetone and 3-pentanone, including their fluorinated and chlorinated derivatives, with performic acid have been studied by ab initio and DFT calculations. Results are compared with experimental findings for the Baeyer−...
A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone
John J. Esteb , J. Nathan Hohman , Diana E. Schlamadinger and Anne M. WilsonJournal of Chemical Education2005 82 (12), 1837A Solvent-Free Baeyer–Villiger Lactonization for the Undergraduate Organic Laboratory: Synthesis of γ-t-Butyl-ε-caprolactone
John J. Esteb , J. Nathan Hohman , Diana E. Schlamadinger and Anne M. WilsonJournal of Chemical Education2005 82 (12), 1837We present an experiment involving the Baeyer–Villiger oxidation reactionfor a first-year organic chemistry class. The Baeyer–Villiger reactionprovides an efficient method to convert ketones to esters or lactones. Most organictextbooks cover the Baeyer–...
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- Received: August 03, 2009
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