Stereochemical and conformational consequences of the oxidation of 1,4-thiazane-3,5-dicarboxylates

Craig A. Hutton; Rania Jaber; Michelle Otaegui; Jennifer J. Turner; Peter Turner; Jonathan M. White; George B. Bacskay

doi:10.1039/B202231A

You do not have JavaScript enabled. Please enable JavaScript to access the full features of the site or access our non-JavaScript page.

Stereochemical and conformational consequences of the oxidation of 1,4-thiazane-3,5-dicarboxylates

Craig A. Hutton,*^a Rania Jaber,^a Michelle Otaegui,^b Jennifer J. Turner,^a Peter Turner,^a Jonathan M. White^b and George B. Bacskay^a

Author affiliations

* Corresponding authors

^a School of Chemistry, The University of Sydney, NSW 2006, Australia
E-mail: c.hutton@chem.usyd.edu.au
Fax: +61 2 9351 3329
Tel: +61 2 9351 2752

^b School of Chemistry, The University of Melbourne, VIC 3010, Australia

Abstract

The stereoselectivity of the oxidation of 1,4-thiazane-3,5-dicarboxylate derivatives to the corresponding sulfoxides and sulfones was found to be dependent on the type of oxidant used and the conformational preference of the substrate. Direct oxidants, such as sodium periodate, peroxides and peracids, preferentially react with the axial sulfur lone-pair, providing the axial S-oxide. Oxidation with bromine–water yielded the epimeric equatorial S-oxide, presumably as a result of initial attack of the axial sulfur lone pair providing the axial bromosulfonium ion, with subsequent displacement of bromide by water leading to the equatorial S-oxide.

Download options Please wait...

Supplementary files

Crystal structure data TXT (27K)

Article information

DOI: https://doi.org/10.1039/B202231A
Article type: Paper
Submitted: 04 Mar 2002
Accepted: 15 Apr 2002
First published: 26 Apr 2002

Download Citation

J. Chem. Soc., Perkin Trans. 2, 2002, 1066-1071

Permissions

Request permissions

Stereochemical and conformational consequences of the oxidation of 1,4-thiazane-3,5-dicarboxylates

C. A. Hutton, R. Jaber, M. Otaegui, J. J. Turner, P. Turner, J. M. White and G. B. Bacskay, J. Chem. Soc., Perkin Trans. 2, 2002, 1066 DOI: 10.1039/B202231A

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Fetching data from CrossRef.
This may take some time to load.

Journal of the Chemical Society, Perkin Transactions 2

Stereochemical and conformational consequences of the oxidation of 1,4-thiazane-3,5-dicarboxylates

Abstract

Supplementary files

Article information

Download Citation

Permissions

Stereochemical and conformational consequences of the oxidation of 1,4-thiazane-3,5-dicarboxylates

Search articles by author

Spotlight

Advertisements