Issue 45, 2012
From the journal:

Organic & Biomolecular Chemistry

Oxygen–sulfur rearrangement in the reaction of thiocarbamate imidazolium ylide with arylaldehyde†

Yingwei Zhao,a   Min Lei,a   Lei Yang,a   Feng Han,a   Zhen Lia  and  Chungu Xia*a  

* Corresponding authors

a State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou, China
E-mail: cgxia@licp.cas.cn
Fax: +86-931-4968129

Abstract

The nucleophilic addition of thiocarbamate imidazolium ylide to aldehyde triggered sequential intramolecular N to O migration of thiocarbonyl amide group and reversible oxygen–sulfur rearrangement to afford 2-imidazolium alkylcarbamothioate. The ortho group on phenyl of aldehyde strongly affects the balance of the O- to S-rearrangement.

Graphical abstract: Oxygen–sulfur rearrangement in the reaction of thiocarbamate imidazolium ylide with arylaldehyde

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C2OB26520F
Article type
Communication
Submitted
02 Aug 2012
Accepted
12 Sep 2012
First published
18 Sep 2012

Org. Biomol. Chem., 2012,10, 8956-8959

Permissions

Request permissions

Oxygen–sulfur rearrangement in the reaction of thiocarbamate imidazolium ylide with arylaldehyde

Y. Zhao, M. Lei, L. Yang, F. Han, Z. Li and C. Xia, Org. Biomol. Chem., 2012, 10, 8956 DOI: 10.1039/C2OB26520F

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.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements