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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH FRONT

Kinetic Study of the Radical Azidation with Sulfonyl Azides*

Karin Weidner A and Philippe Renaud A B

A University of Bern, Department of Chemistry and Biochemistry, Freiestrasse 3, CH-3012 Bern, Switzerland.

B Corresponding author. Email: philippe.renaud@ioc.unibe.ch

Australian Journal of Chemistry 66(3) 341-345 http://dx.doi.org/10.1071/CH12523
Submitted: 25 November 2012  Accepted: 18 December 2012   Published: 25 January 2013

Abstract

Rate constants for the reaction between a secondary alkyl radical and two different sulfonyl azides were determined using bimolecular competing radical reactions. The rates of azidation were determined by competition with hydrogen atom transfer from tris(trimethylsilyl)silane ((TMS)3SiH) of the 4-phenylcyclohexyl radical. 3-Pyridinesulfonyl azide and trifluoromethanesulfonyl azide were found to have rate constants for azidation of 2 × 105 M–1 s–1 and 7 × 105 M–1 s–1 at 80°C, respectively.

Graphical Abstract Image


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