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  Home > JCE Print > Journal of Chemical Education > Issues > 1998  > October  >
In the Laboratory
Use of Theoretical Chemistry To Explain Baeyer-Villiger Oxidations of Methoxy Aromatic Aldehydes
N. Anoune, H. Hannachi, P. Lantéri, R. Longeray, and C. Arnaud
Laboratoire de Chimiométrie et Synthèse Organique, CPE-Lyon, 43 Boulevard du 11 Novembre 1918, Villeurbanne Cedex F. 69622, France
Cover
October 1998
Vol. 75 No. 10
p. 1290
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.
More Information
*  Citation
 Anoune, N.; Hannachi, H.; Lantéri, P.; Longeray, R.; Arnaud, Christian. J. Chem. Educ. 1998 75 1290.
*  Keywords
 organic chem, mechanisms, theoretical chem, laboratory instruction
*  History
 Created:
Last Updated:		 June 21, 1999
June 24, 2005
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