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Paper | Regular issue | Vol 68, No. 4, 2006, pp.701-712
Published online, 10th March, 2006
DOI: 10.3987/COM-06-10667
1,3-Dibromo-5,5-dimethylhydantoin as a New Imidazolidine Dehydrogenating Agent: Synthesis of 4,5-Dihydro-1H-imidazolium Salts

María C. Caterina, María A. Figueroa, Isabel A. Perillo, and Alejandra Salerno*

*Department of Organic Chemistry, Faculty of Pharmacy and Biochemistry, University of Buenos Aires, Junín 956 (1113) Buenos Aires, Argentina

Abstract

A study about the scope of the method for the attainment of 4,5-dihydro-1H-imidazolium salts by dehydrogenation of N,N’-dibenzyl- and N-aryl-N’-benzylimidazolidines is presented. Employed dehydrogenating agents were N-bromoacetamide (NBA), N-bromosuccinimide (NBS), carbon tetrachloride and 1,3-dibromo-5,5-dimethylhydantoin (DBDMH). DBDMH was the choice reagent due to the purity of the attained products, lowest reaction times and highest yields.