Cover Picture: Iodine(III)‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State (Chem. Eur. J. 4/2004)

Cover Picture: Iodine(III)‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives:... Cover Picture Dominique Leca, Kai Song, Muriel Amatore, Louis Fensterbank, Emmanuel LacÙte, and Max Malacria The cover picture shows the iodine-mediated one-pot stereoselective synthesis of a chiral sulfonimidate starting from a sulfinamide in the presence of methanol. The X- ray diffraction structure determination of the major diastereoisomer indicated that the reaction mainly occurred with retention of configuration, presumably through an early intermediate, which was transformed following two different pathways. Rear- rangement via a four-atom transition state afforded sulfonimidates with retention of configuration. A competitive three-atom rearrangement would cause the partial race- mization. A discussion of these proposals, as well as the synthesis of free sulfonimi- dates and a convenient preparation of sulfoximines and sulfonamides are described by Malacria et al. on p. 906 ff. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Chemistry - A European Journal Wiley

Cover Picture: Iodine(III)‐Mediated Preparations of Nitrogen‐Containing Sulfur Derivatives: Dramatic Influence of the Sulfur Oxidation State (Chem. Eur. J. 4/2004)

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Publisher
Wiley
Copyright
Copyright © 2004 Wiley Subscription Services, Inc., A Wiley Company
ISSN
0947-6539
eISSN
1521-3765
DOI
10.1002/chem.200490011
Publisher site
See Article on Publisher Site

Abstract

Cover Picture Dominique Leca, Kai Song, Muriel Amatore, Louis Fensterbank, Emmanuel LacÙte, and Max Malacria The cover picture shows the iodine-mediated one-pot stereoselective synthesis of a chiral sulfonimidate starting from a sulfinamide in the presence of methanol. The X- ray diffraction structure determination of the major diastereoisomer indicated that the reaction mainly occurred with retention of configuration, presumably through an early intermediate, which was transformed following two different pathways. Rear- rangement via a four-atom transition state afforded sulfonimidates with retention of configuration. A competitive three-atom rearrangement would cause the partial race- mization. A discussion of these proposals, as well as the synthesis of free sulfonimi- dates and a convenient preparation of sulfoximines and sulfonamides are described by Malacria et al. on p. 906 ff.

Journal

Chemistry - A European JournalWiley

Published: Aug 20, 2005

Keywords: ; ; ; ;

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