Facile one-pot synthesis of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent
A new method for the preparation of α-bromoketones from olefins using bromide/bromate couple as a nonhazardous brominating agent has been developed. Several α-bromoketones were successfully prepared from a variety of olefins by this method. This procedure is an alternative to conventional molecular bromine.
Patil, Rajendra D.,Joshi, Girdhar,Adimurthy, Subbarayappa,Ranu, Brindaban C.
experimental part
p. 2529 - 2532
(2009/09/06)
ELECTRON TRANSFER IN REACTIONS OF tert-PERFLUOROALKYL BROMIDES WITH ALKENES AND NUCLEOPHILES
Tertiary perfluoroalkyl bromides (RFBr) in nonpolar solvents under mild conditions can be added to the multiple bond of terminal alkenes, alkynes, and butadiene.Slow addition to alkenes at 20 deg C is accelerated in proton-donating solvents and is catalyzed by readily oxidizable nucleophiles.Bromination of the multiple bond and formation of RFBr reduction products suggests a radical-chain mechanism initiated by electron transfer to the RFBr molecule.