Hydrogen peroxide-or sodium hypochlorite-induced bromination of 1-arylbut-2-enes

Sadygov, O. A.; Alimardanov, Kh. M.

doi:10.1134/s1070428007110139

Cited by 6 publications

(5 citation statements)

References 4 publications

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“…Treatment of 1-arylbut-2-enes using a mixture of HBr and H 2 O 2 leads to electrophilic addition of bromine or hypobromous acid at the side chain double bond (Scheme ). Under more severe conditions, the process is accompanied by the bromination of the aromatic ring …”

Section: Bromination Reactionsmentioning

confidence: 89%

“…Under more severe conditions, the process is accompanied by the bromination of the aromatic ring. 1270 Again, treatment of the 1-arylbut-2-enes with peroxy acids (RCOOH−H 2 O 2 ) gives the corresponding epoxy derivatives, which react with HBr and oxygen-containing nucleophiles to produce α-bromo alcohols (Scheme 448).…”

Section: Espenson Et Al Tried Methyltrioxorhenium (Mto) Catalysis In ...mentioning

confidence: 99%

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Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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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.

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Section: Bromination Reactionsmentioning

confidence: 89%

Section: Espenson Et Al Tried Methyltrioxorhenium (Mto) Catalysis In ...mentioning

confidence: 99%

Use of Bromine and Bromo-Organic Compounds in Organic Synthesis

2016

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“…It will react directly with the hydrogen peroxide and form peracetic acid. This will then in turn oxidise the bromide in a reaction similar to Equation (9) [28a,42] . However, some research suggests that this formation of peracetic acid can lead to the subsequent formation of AcOBr, a more potent brominating agent [43] .…”

Section: Peroxidesmentioning

confidence: 99%

“…Solid 4Na 2 SO 4 ⋅ 2H 2 O 2 ⋅ NaCl crystals can also be used to produce peracetic acid, which can then be used for oxidative bromination or immediately as an oxidant [23] . Caution has to be taken with peracetic acid, since it can also epoxidise a double bond rather than brominating it [28a] …”

Section: Peroxidesmentioning

confidence: 99%

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Bromide Oxidation: A Safe Strategy for Electrophilic Brominations

2022

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Bromination of organic substances is still an important reaction in modern synthetic chemistry. In view of the increasing demand for sustainable synthetic chemistry, oxidative bromination can play an important role to avoid the use of hazardous molecular bromine (Br 2 ). In this review, a complete overview of the chemical oxidants will be provided which have been used for the electrophilic as well as radical brominations, starting from less hazardous bromide Br(À I); e. g., HBr or a bromide salt, with a focus on the differences caused by the choice of oxidant.

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