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Tribromoisocyanuric Acid as a Green Cohalogenating Reagent: An Efficient Transformation of Alkynes into α,α-Dibromoketones and Vicinal Dibromoalkenes

Author(s):

Livia Crespo, Monica R. Senra, Pierre Esteves and Marcio de Mattos*   Pages 1 - 6 ( 6 )

Abstract:


The co-halogenation reaction of alkynes with tri-bromoisocyanuric acid in acetic acid, followed by aqueous work-up produced α,α-di-bromoketones (44-84%), while the reaction in aqueous acetonitrile in the presence of KBr produced vicinal di-bromoalkenes (66-86%). The usefulness of the methodology was demonstrated employing green metrics for the comparison of TBCA with analogous N-halo reagents in co-halogenation reactions of alkynes.

Keywords:

Bromination, Electrophilic addition, Halogenation, Regioselectivity, Green chemistry, Alkenes, Alkynes, Ketones

Affiliation:

Universidade Federal do Rio de Janeiro, Departamento de Quimica Organica, Universidade Federal do Rio de Janeiro, Departamento de Quimica Organica, Universidade Federal do Rio de Janeiro, Departamento de Quimica Organica, Universidade Federal do Rio de Janeiro, Departamento de Quimica Organica



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