“…The selection of bromo-organic compounds in this work is based primarily on their potential for bromination reactions. This work summarizes the applications of the following bromo-organic compounds in organic synthetic transformations: (1) Nbromosuccinimide, (2) ammonium bromide, (3) N-bromoacetamide, (4) bis(dimethylacetamide) hydrogen dibromobromate, (5) benzalkonium tribromide (6) 1-benzyl-4-aza-1azoniabicyclo[2.2.2]octane tribromide, (7) benzimidazolium bromochromate, (8) benzyltriethylammonium tribromide, (9) benzyltrimethylammonium tribromide, (10) benzyltriphenylphosphonium tribromide, (11) bromamine-T, (12) Nbromobenzamide (benzbromamide), ( 13) N-bromo-tert-butylamine, ( 14) 2-bromo-2-cyano-N,N-dimethylacetamide, (15) bromodichloroisocyanuric acid, ( 16) 1-bromo-5,5-diethylbarbituric acid and 1,3-dibromo-5,5-diethylbarbituric acid, (17) bromodimethylsulfonium bromide, (18) 3-bromo-4,4-dimethyl-2-oxazolidinone, (19) 3-bromo-5,5-dimethylhydantoin, (20) 3-bromo-3-(ethoxycarbonyl)-2,4-dioxo-1,2,3,4-tetrahydroquinones, (21) bromonitromethane, ( 22) N-bromophthalimide, (23) N-bromosaccharin, (24) (tert-butylamino)triphenylphosphonium tribromide, (25) tert-butyl N,N-dibromocarbamate, (26) 1-butyl-3-methylimidazolium tribromide, (27) 1-butyl-3methylpyridinium tribromide, (28) bromine supported on resin, (29) carbon tetrabromide, (30) cetylpyridinium tribromide, (31) cetyltrimethylammonium tribromide, (32) chiral brominating agent, (33) cross-linked poly(vinylpyridinium hydrobromide perbromide) resins, (34) crown ether complex of molecular bromine, (35) Apart from the above bromo-organic compounds, we also discuss herein the use of different nonmetallic as well as naturally occurring bromo compounds in synthetic organic transformations: (109) HOBr, (110) phosphorus oxybromide, (111) iodine monobromide, (112) boron tribromide, (113) bromine chloride, (114) thionyl bromide, (115) bromine fluoride, (116) bromine trifluoride, (117) HBr, (118) bromoiodinanes, (119) alkyl hypobromites...…”
Section: Scope Of This Reviewmentioning
confidence: 99%
“…Reactions of 2-oxaadamantane with Br 2 /AlBr 3 , HNO 3 , CrO 3 /Ac 2 O, and Pb(OAc) 4 introduced substituents into positions remote from the oxa bridge. 117 Wei et al provided a one-pot process for the preparation of ritodrine hydrochloride, which comprised bromination of 1-(4-methoxyphenyl)-1-propanone with Br 2 to obtain 2-bromo-4′-methoxypropiophenone, followed by reaction with 4-Methoxybenzeneethanamine, hydrolysis in 48% hydrobromic acid, reduction with boron compounds, and addition of hydrochloric acid to give the product. The process has the advantages of a low cost, a short reaction time, and a high product yield.…”
Section: Bromination Reactions 31 Bromination With Molecular Brominementioning
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.
“…The selection of bromo-organic compounds in this work is based primarily on their potential for bromination reactions. This work summarizes the applications of the following bromo-organic compounds in organic synthetic transformations: (1) Nbromosuccinimide, (2) ammonium bromide, (3) N-bromoacetamide, (4) bis(dimethylacetamide) hydrogen dibromobromate, (5) benzalkonium tribromide (6) 1-benzyl-4-aza-1azoniabicyclo[2.2.2]octane tribromide, (7) benzimidazolium bromochromate, (8) benzyltriethylammonium tribromide, (9) benzyltrimethylammonium tribromide, (10) benzyltriphenylphosphonium tribromide, (11) bromamine-T, (12) Nbromobenzamide (benzbromamide), ( 13) N-bromo-tert-butylamine, ( 14) 2-bromo-2-cyano-N,N-dimethylacetamide, (15) bromodichloroisocyanuric acid, ( 16) 1-bromo-5,5-diethylbarbituric acid and 1,3-dibromo-5,5-diethylbarbituric acid, (17) bromodimethylsulfonium bromide, (18) 3-bromo-4,4-dimethyl-2-oxazolidinone, (19) 3-bromo-5,5-dimethylhydantoin, (20) 3-bromo-3-(ethoxycarbonyl)-2,4-dioxo-1,2,3,4-tetrahydroquinones, (21) bromonitromethane, ( 22) N-bromophthalimide, (23) N-bromosaccharin, (24) (tert-butylamino)triphenylphosphonium tribromide, (25) tert-butyl N,N-dibromocarbamate, (26) 1-butyl-3-methylimidazolium tribromide, (27) 1-butyl-3methylpyridinium tribromide, (28) bromine supported on resin, (29) carbon tetrabromide, (30) cetylpyridinium tribromide, (31) cetyltrimethylammonium tribromide, (32) chiral brominating agent, (33) cross-linked poly(vinylpyridinium hydrobromide perbromide) resins, (34) crown ether complex of molecular bromine, (35) Apart from the above bromo-organic compounds, we also discuss herein the use of different nonmetallic as well as naturally occurring bromo compounds in synthetic organic transformations: (109) HOBr, (110) phosphorus oxybromide, (111) iodine monobromide, (112) boron tribromide, (113) bromine chloride, (114) thionyl bromide, (115) bromine fluoride, (116) bromine trifluoride, (117) HBr, (118) bromoiodinanes, (119) alkyl hypobromites...…”
Section: Scope Of This Reviewmentioning
confidence: 99%
“…Reactions of 2-oxaadamantane with Br 2 /AlBr 3 , HNO 3 , CrO 3 /Ac 2 O, and Pb(OAc) 4 introduced substituents into positions remote from the oxa bridge. 117 Wei et al provided a one-pot process for the preparation of ritodrine hydrochloride, which comprised bromination of 1-(4-methoxyphenyl)-1-propanone with Br 2 to obtain 2-bromo-4′-methoxypropiophenone, followed by reaction with 4-Methoxybenzeneethanamine, hydrolysis in 48% hydrobromic acid, reduction with boron compounds, and addition of hydrochloric acid to give the product. The process has the advantages of a low cost, a short reaction time, and a high product yield.…”
Section: Bromination Reactions 31 Bromination With Molecular Brominementioning
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.
“…The observed stereochemistry of 27 can be explained by the intermediate formation of hydroxyorthoacetate 26 , which could be specifically cleaved by protonation on the ether oxygen. Acetates 27 and 28 , as well as 18 (Scheme ), were easily transformed to oxadamantane in sulfuric acid. , 1 Thermal ellipsoid plot of endo,endo -7-acetoxy-3-hydroxybicyclo[3.3.1]nonane ( 27 ).…”
Section: Resultsmentioning
confidence: 99%
“…2-Oxaadamantane (2). ,, (a) Hydroxyacetate 27 (0.1 g, 0.5 mmol) was added to the 95% sulfuric acid (65 g) at 0 °C, and the reaction was stirred for 0.5 h and then poured into H 2 O and extracted with CH 2 Cl 2 (4 × 10 mL). The combined organic extracts were washed with 5% aqueous NaHCO 3 and dried over anhydrous Na 2 SO 4 .…”
Section: Methodsmentioning
confidence: 99%
“…This would parallel the known double Criegee rearrangement of ketals, which proceeds through the corresponding ortho esters and, ultimately, to oxacycloalkanes. If the web of O-insertion reactions from 1 to 2 and 3 could be untangled, a new controllable pathway of bicyclo[3.3.1]nonane and oxaadamantane synthesis could be achieved.…”
Selective oxidative cleavage-cyclization of adamantane through the bridge carbon was developed in trifluoroperacetic acid (TFPAA). The methyl group in the bridge position was found to be the substituent that directs consecutive oxygen insertion into the cage structure during the course of a Criegee rearrangement. The formation of stable 5-methyl-4,6-dioxabishomoadamant-5-yl cation at -25 degrees C was observed. Stable carboxonium ion formation allows control of the selectivity of further transformations. Hydrolysis leads to the stereospecific formation of endo,endo-3-hydroxy-7-acetoxybicyclo[3.3. 1]nonane. Its single-crystal X-ray structure was obtained. An increase in temperature results in deprotonation of the 5-methyl-4, 6-dioxabishomoadamant-5-yl cation to endo-3-trifluoroacetoxybicyclo[3.3.1]non-6-ene, which undergoes further epoxidation with TFPAA and acidic transannular cyclization in trifluoroacetic acid (TFAA). The described reactions can be used as a convenient method for the synthesis of bicyclo[3.3.1]nonane and oxaadamantane derivatives. The proposed mechanism for each transformation, as well as supporting ab initio theoretical calculations of the strain energy and the stabilization energy of the relevant oxacage structures, are discussed.
Die Bromierung aliphatischer Verbindungen mit NaOH/CBr4 unter Phasentransferbedingungen liefert selektiv tertiäre Bromide. Fehlen tertiäre C‐H‐Bindungen im Molekül, so werden auch sekundäre aktiviert (siehe oben). Dieses konzeptionell neue Reaktionssystem zur C‐H‐Aktivierung wird sehr wahrscheinlich durch einen Einelektronentransfer eingeleitet und durch eine radikalische Substitution mit hoher Regioselektivität abgeschlossen.
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