Issue 1, 2009

Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

Abstract

Various alkenes (internal, terminal, aryl and alkyl substituted) and 1,2-diphenylethyne were efficiently and selectively dibrominated using 2 equivalents of 48% aqueous hydrobromic acid, with air as an oxidant and sodium nitrite as a catalyst. Despite the presence of water, only trans dibromination occurred producing anti-1,2-dibromoalkanes and (E)-1,2-dibromo-1,2-diphenylethene. A comparison of resource demand, waste production and environmental, health and safety issues of the NaNO2 catalyzed aerobic bromination with molecular bromine and other oxidative bromination methods revealed that the proposed method is not only selective and effective but has a better environmental profile.

Graphical abstract: Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

Supplementary files

Article information

Article type
Paper
Submitted
28 Aug 2008
Accepted
15 Oct 2008
First published
17 Nov 2008

Green Chem., 2009,11, 120-126

Selective aerobic oxidative dibromination of alkenes with aqueous HBr and sodium nitrite as a catalyst

A. Podgoršek, M. Eissen, J. Fleckenstein, S. Stavber, M. Zupan and J. Iskra, Green Chem., 2009, 11, 120 DOI: 10.1039/B814989E

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