M. Goodman, M. Detty
May 7, 2004
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0
Influential Citations
51
Citations
Journal
Organometallics
Abstract
Diphenyl selenoxide (7), dibenzyl selenoxide (8), and several aryl benzyl selenoxides (9−13) are catalysts for the bromination of organic substrates in two-phase systems of CH2Cl2 and pH 6 phosphate buffer containing 2.0 M NaBr and 2.6 M H2O2. The catalysts are effective at 2.5 mol % relative to the organic substrates. In the bromination of 4-pentenoic acid, electron-donating substituents in the selenoxides accelerate the reaction, while electron-withdrawing substituents slow the reaction. Benzyl 2-((dimethylamino)methyl)phenyl selenoxide (13), with a chelating dimethylamino group, was the most effective catalyst and was used in the preparative bromination of 4-pentenoic acid, 2,2-diphenyl-4-pentenoic acid, 1,3,5-trimethoxybenzene, N,N-dimethylaniline, and N-phenylmorpholine.