Unusual behaviour of N-bromosuccinimide. Conversion of N,N-dimethylamides to N-methyl,N-succinimidomethylamides

Caristi, Corrado; Cimino, Giuseppe; Ferlazzo, A; Gattuso, Mario; Parisi, Melchiorre F.

doi:10.1016/s0040-4039(00)87977-0

Cited by 7 publications

(6 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Caristi and co-workers reported that N , N -dimethyl amides can be converted to N -succinimidomethyl amides by treatment with NBS in almost quantitative yield . The reaction was carried out in CCl 4 in the presence of benzoyl peroxide in reflux conditions (Scheme ).…”

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

View full text Add to dashboard Cite

Bromination is one of the most important transformations in organic synthesis and can be carried out using bromine and many other bromo compounds. Use of molecular bromine in organic synthesis is well-known. However, due to the hazardous nature of bromine, enormous growth has been witnessed in the past several decades for the development of solid bromine carriers. This review outlines the use of bromine and different bromo-organic compounds in organic synthesis. The applications of bromine, a total of 107 bromo-organic compounds, 11 other brominating agents, and a few natural bromine sources were incorporated. The scope of these reagents for various organic transformations such as bromination, cohalogenation, oxidation, cyclization, ring-opening reactions, substitution, rearrangement, hydrolysis, catalysis, etc. has been described briefly to highlight important aspects of the bromo-organic compounds in organic synthesis.

show abstract

Section: Miscellaneous Reactionsmentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

“…N -Methyl- N -succinimidomethylacetoamide ( 2a ) is known as a radical reaction product of NBS with DMA (Scheme ) . We synthesized 2a as an authentic compound by a method in the literature . We obtained N -methyl- N -succinimidomethylformamide ( 2b ) as the coupling product of DMF by the same reaction procedure.…”

Section: Resultsmentioning

confidence: 99%

Incompatibilities between N-Bromosuccinimide and Solvents

Shimizu

Imamura

Ueki

2014

Org. Process Res. Dev.

View full text Add to dashboard Cite

Incompatibilities between N-bromosuccinimide (NBS) and solvents were examined by measuring the heat of reaction by an advanced reactive system screening tool (ARSST) and a reaction calorimeter (RC1e). The ARSST experiments showed that amides, THF, and toluene solutions require consideration of incompatibilities with NBS. Isothermal analyses by RC1e revealed accurate heats of incompatibilities and the autocatalytic behaviors of the incompatibilities. Experiments in the presence of a radical initiator or inhibitor demonstrated that the incompatibility is caused by the radical mechanism and the incompatibility is increased by the presence of radical initiators. Further experiments made clear that DBDMH, an alternative brominating reagent, showed behavior similar to that of NBS.

show abstract

“…Indeed, the Parisi group has reported that N,Ndimethylamides can convert NBS to Br 2 . 21 The Braddock group also demonstrated that DMF and DMA can behave as nucleophilic organocatalysts for the transfer of electrophilic bromine from NBS. 22 Moreover, highly enantioselective electrophilic brominations catalyzed by peptides, and Lewis base catalyzed alkene halofunctionalizations, were reported recently by Miller and Denmark, respectively.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Bromine-Catalyzed Conversion of CO₂ and Epoxides to Cyclic Carbonates under Continuous Flow Conditions

Kozak

et al. 2013

J. Am. Chem. Soc.

136

View full text Add to dashboard Cite

A continuous method for the formation of cyclic carbonates from epoxides and carbon dioxide (CO2) is described. The catalysts used are inexpensive and effective in converting the reagents to the products in a residence time (t(R)) of 30 min. The cyclic carbonate products are obtained in good to excellent yield (51-92%). On the basis of a series of kinetics experiments, we propose a reaction mechanism involving epoxide activation by electrophilic bromine and CO2 activation by an amide.

show abstract

Unusual behaviour of N-bromosuccinimide. Conversion of N,N-dimethylamides to N-methyl,N-succinimidomethylamides

Cited by 7 publications

References 6 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Incompatibilities between N-Bromosuccinimide and Solvents

Bromine-Catalyzed Conversion of CO₂ and Epoxides to Cyclic Carbonates under Continuous Flow Conditions

Contact Info

Product

Resources

About

Unusual behaviour of N-bromosuccinimide. Conversion of N,N-dimethylamides to N-methyl,N-succinimidomethylamides

Cited by 7 publications

References 6 publications

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

Incompatibilities between N-Bromosuccinimide and Solvents

Bromine-Catalyzed Conversion of CO2 and Epoxides to Cyclic Carbonates under Continuous Flow Conditions

Contact Info

Product

Resources

About

Bromine-Catalyzed Conversion of CO₂ and Epoxides to Cyclic Carbonates under Continuous Flow Conditions