DBDMH is a cheap and convenient alternative to NBS (N-bromosuccinimide) for example for the bromination of electron-rich arenes.
Organocatalytic stereospecific dibromination of various functionalized alkenes was achieved using a simple thiourea catalyst and 1,3-dibromo 5,5-dimethylhydantoin as a stable, inexpensive halogen source at room temperature. The procedure was extended to alkynes and aromatic rings and to dichlorination reactions by using the 1,3-dichloro hydantoin derivative.
G. Hernández-Torres, B. Tan, C. F. Barbas III, Org. Lett., 2012, 14, 1858-1861.
Treatment of methylarenes with 1,3-dibromo-5,5-dimethylhydantoin or N-bromosuccinimide and a catalytic amount of 2,2′-azobis(isobutyronitrile) followed by a reaction with a nucleophile, such as benzoic acid, p-toluenethiol, sodium p-toluenesulfinate, aqueous dimethylamine, or succinimide, provides the corresponding benzylated products in good yields.
H. Shimojo, K. Moriyama, H. Togo, Synthesis, 2015, 47, 1280-1290.
A mild and efficient oxidation of various thiols affords the corresponding disulfides using 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) as oxidant under both solution and solvent-free conditions.
A. Khazaei, M. A. Zolfigol, A. Rostami, Synthesis, 2004, 2959-2961.
A mild and efficient method enables the formation of methylene acetals from 1,2- and 1,3-diols using methoxymethylphenylsulfide, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and dibutylhydroxytoluene (BHT). The use of BHT suppresses side reactions and enables high-yielding formation of methylene acetals of various diols, including carbohydrate-type substrates.
T. Maegawa, Y. Koutani, K. Otake, H. Fujioka, J. Org. Chem., 2013, 78, 3384-3390.
An oxidative rearrangement of 3-aminoindazoles provides diversely functionalized 1,2,3-benzotriazine-4(3H)-ones in good yields at room temperature. Water as cosolvent facilitates the halogen-induced ring expansion of 3-aminoindazoles under oxidative conditions.
Y. Zhou, Y. Wang, Y. Lou, Q. Song, Org. Lett., 2018, 20, 6494-6497.