New Aspects on the Preparation of 1,3-Dibromo-5,5-dimethylhydantoin

Markish, Itzhak; Arrad, Onn

doi:10.1021/ie00045a022

Cited by 11 publications

(8 citation statements)

References 3 publications

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“…14.9 ± 0.1 1 -14 [58] 9.25 ± 0.05 9.16 ± 0.02 Values were not found DMH, 5,5-dimethylhydantoin; MDMH, 1-hydroximethyl-5,5-dimethylhydantoin. 1 This value is not accurate.…”

Section: Hydrolysis Of N-chloro-hydantoins Formedmentioning

confidence: 93%

“…Second-order rate constants for the formation reaction of 3-chloro-5,5-dimetylhydantoin and 3-chloro-1hydroximethyl-5,5-dimethylhydantoin with HOCl Hydantoins + HOCl k 2 /M À1 s À1 (HOCl + RN À ) (7.5 ± 0.4) × 10 6 (10.1 ± 0.2) × 10 6 k 3 /M À1 s À1 (ClO À + RNH) (1.53 ± 0.08) × 10 5 (1.27 ± 0.02) × 10 5 pK 2 (RNH ⇄ RN À + H + ) 9.16 ± 0.08 9.37 ± 0.2 DMH, 5,5-dimethylhydantoin; MDMH, 1-hydroximethyl-5,5dimethylhydantoin. [32] 9.00 [58] 9.19 [59,60] 9.20 [61] H in position 1…”

Section: Hydrolysis Of N-chloro-hydantoins Formedmentioning

confidence: 99%

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N-Chlorination rate of five-membered heterocyclic nitrogen compounds

Pastoriza

Antelo

Amoedo

et al. 2016

J. Phys. Org. Chem.

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aThe kinetics of N-chlorination reaction of pyrrolidine, pyrrolidone, succinimide, 5,5,-dimethyloxazolidine-2,4-dione, 5,5-dimethylhydantoin and 1-hydroximethyl-5,5-dimethylhydantoin with HOCl in aqueous solution were studied at 25°C, constant ionic strength and under isolation conditions in a wide pH range. The set of compounds studied in this paper is characterized by having different functional groups and the same cyclic structure, consisting of a five-member ring with a nitrogen atom in the ring, which is susceptible to be chlorinated. This series of compounds covers nine pK a units, and the kinetic studies allow us to know, like, the presence of an amino, amide or imide group modify the reactivity of nitrogenous compound.Experimental data were fitted to the first-order kinetic equation. All reactions were found to be of first order in both HOCl and nitrogenous compound concentration. Kinetics studies demonstrate that some of these compounds are hydrolyzed in alkaline medium. In each case, reaction mechanism in agreement with the experimental results is proposed. The results were compared with other compounds with similar cyclic structure (2-oxazolidinone and proline).

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“…14.9 ± 0.1 1 -14 [58] 9.25 ± 0.05 9.16 ± 0.02 Values were not found DMH, 5,5-dimethylhydantoin; MDMH, 1-hydroximethyl-5,5-dimethylhydantoin. 1 This value is not accurate.…”

Section: Hydrolysis Of N-chloro-hydantoins Formedmentioning

confidence: 93%

Section: Hydrolysis Of N-chloro-hydantoins Formedmentioning

confidence: 99%

N-Chlorination rate of five-membered heterocyclic nitrogen compounds

Pastoriza

Antelo

Amoedo

et al. 2016

J. Phys. Org. Chem.

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“…The 1,3-dibromo-5,5-dimethylhydantoin (DBDMH or DBH) is a useful reagent for various organic transformations 18–20 including aromatic bromination. 21–25 Enhanced reactivity of DBH towards aromatic bromination in the presence of acids has been noted.…”

mentioning

confidence: 99%

Bromination at C-5 of pyrimidine and C-8 of purine nucleosides with 1,3-dibromo-5,5-dimethylhydantoin

Rayala

Wnuk

2012

Tetrahedron Letters

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Treatment of the protected and unprotected nucleosides with 1,3-dibromo-5,5- dimethylhydantoin in aprotic solvents such as CH2Cl2, CH3CN, or DMF effected smooth bromination of uridine and cytidine derivatives at C-5 of pyrimidine rings as well as adenosine and guanosine derivatives at C-8 of purine rings. Addition of Lewis acids such as trimethylsilyl trifluoromethanesulfonate enhanced efficiency of bromination.

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“…(1), it is difficult to explain the decrease in pH in the hydrolysis process, as the products HBrO and DMH are only very weak acids. 9 However it is possible that hypobromic acid could undergo further decomposition to form Br2 and strong acid HBrO3:…”

mentioning

confidence: 99%