cas 618-32-6, Benzoyl bromide | Articles data

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Benzoyl halide as alternative precursor for synthesis of lead free double perovskite Cs3Bi2Br9 nanocrystals
Ternary bismuth halides are interesting functional materials closely related to Pb halide perovskite photovoltaic material, and are widely sought after due to reduced toxicity of Bi compared to Pb. There are several reports on synthesis of Cs3Bi2Br9 nanocrystals (NCs) due to its being relatively stable compared to lead perovskite. Cs3Bi2Br9 nanocrystals have been synthesised using benzoyl bromide as an precursor using hot injection process at two different temperatures of 120 °C and 160 °C. Samples have been characterized for its structural, optical, microstructural and luminescent properties using X-ray diffraction, (XRD) UV-Vis spectroscopy, high resolution transmission electron microscopy and photoluminescent spectroscopy. XRD showed formation of Cs3Bi2Br9 phase with mono-crystalline structure. UV-Vis showed two types of band gap in the visible region which shows that the material can be used for photovoltaic applications. HRTEM confined the particles to be composed of nanocrystals with ～5 nm particles in the samples grown at 120 °C and it the particles joined together yield various structures composed of nanoparticles. The time resolved photoluminescence shows average life times of 3.067 ns and 4.761 ns for samples grown at two different temperatures. To the best of our knowledge, this is the first report where benzoyl halide has been used as alternative precursor for the synthesis of lead free double perovskite Cs3Bi2Br9 nanocrystals which have many applications.
Kumar, Ashish,Rawat, S. S.,Singh, Vidya Nand,Srivastava, Ritu,Swami, Sanjay Kumar
p. 3802 - 3808
(2020)
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Cross-dehydrogenative coupling of acetanilides with aromatic aldehydes
Potassium bromide mediated cross-dehydrogenative coupling of acetanilides with aromatic aldehydes in the presence of tert-butyl hydroperoxide (TBHP) for the synthesis of imides has been developed. This new and efficient approach was carried out under an air atmosphere at room temperature and the desired products were obtained in good to high yields.
Kianmehr, Ebrahim,Afaridoun, Hadi
p. 4319 - 4323
(2020/03/26)

Aerobic oxidative esterification and thioesterification of aldehydes using dibromoisocyanuric acid under mild conditions: No metal catalysts required
A practical direct method for the direct preparation of esters and thioesters from aldehydes is described. Esters and thioesters were synthesized by oxidative esterification and thioesterification via in situ generated acyl bromide intermediates, which were used to react with various alcohols and thiols. The esterification and thioesterification were readily performed in the presence of dibromoisocyanuric acid in dichloromethane, without any metal catalysts and under mild conditions. By using this reaction protocol, various esters and thioesters were prepared in high yields. This effective method offers a promising approach for the facile esterification and thioesterification of aldehydes.
Kwon, Young-Do,La, Minh Thanh,Kim, Hee-Kwon
p. 10833 - 10841
(2018/07/05)

Convenient metal-free direct oxidative amidation of aldehyde using dibromoisocyanuric acid under mild conditions
A facile method for the direct synthesis of amides from aldehydes is described. Amide bonds were synthesized by an oxidative amidation in the presence of dibromoisocyanuric acid (DBI). Treatment of aromatic and aliphatic aldehydes with dibromoisocyanuric acid generated acyl bromide intermediates, which were employed to react with a variety of secondary and primary amines to give amides. Through this reaction method, various amides were synthesized directly from aldehydes under mild conditions in high yields and short times. This facile and efficient procedure provides potential strategy for the direct synthesis of amides from aldehydes.
Kang, Soosung,La, Minh Thanh,Kim, Hee-Kwon
supporting information
p. 3541 - 3546
(2018/08/29)

Appel reaction of carboxylic acids with tribromoisocyanuric acid/triphenylphosphine: A mild and acid-free preparation of esters and amides
A facile and efficient method for esterification and amidation of carboxylic acids under neutral conditions has been developed. Esters and amides can be prepared by reacting a carboxylic acid (1 mmol) with tribromoisocyanuric acid (0.37 mmol) and triphenylphosphine (1 mmol) in dichloromethane at room temperature, followed by addition of an alcohol or an amine, respectively.
Da Cunha Sindra, Haryadylla,De Mattos, Marcio C.S.
p. 1129 - 1136
(2016/07/06)

Environmentally friendly procedure for the aqueous oxidation of benzyl alcohols to aldehydes with dibromodimethylhydantoin (DBDMH) and cyclodextrin: Scope and mechanistic insights
Reported herein is an environmentally friendly procedure for the oxidation of benzyl alcohols to aldehydes using an inexpensive, commercially available reagent, 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), and a variety of cyclodextrin additives under fully aqueous solvent conditions. This reaction proceeds with moderate to good yields for a broad scope of benzyl alcohol substrates, with the cyclodextrin acting to enhance the desired reactivity and limit undesired aromatic bromination side products. The reported experiments provide substantial mechanistic insight that will drive further reaction optimization and have broad-reaching applications.
Chaudhuri, Sauradip,Zaki, Hossam,Levine, Mindy
supporting information
p. 636 - 644
(2016/06/06)

METHOD FOR PRODUCING a-HALO-TETRAACYL-GLUCOSE
There is provided an efficient and excellent preparation method of an α-halo-tetraacyl-glucose which is suitable for industrial preparation, which comprises reacting D-glucose or lower alkyl D-glucoside with a reactive derivative of a carboxylic acid and a metal halide to prepare the α-halo-tetraacyl-glucose represented by the formula (III): wherein R represents an optionally substituted lower alkyl group or an optionally substituted aryl group, and X represents a halogen atom, in one step, and the resulting α-halo-tetraacyl-glucose (III) can be converted into a compound of the formula (I) or a salt thereof by subjecting to a conventional method.
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(2016/01/29)

Design and synthesis of thiazole derivatives as potent FabH inhibitors with antibacterial activity
Components of fatty acid biosynthetic pathway have been identified as attractive targets for the development of new antibacterial agents. Compounds of series A (4a-4g) and series B (5a-5g) were synthesized by the formation of an amine bond between aromati
Li, Jing-Ran,Li, Dong-Dong,Wang, Rong-Rong,Sun, Jian,Dong, Jing-Jun,Du, Qian-Ru,Fang, Fei,Zhang, Wei-Ming,Zhu, Hai-Liang
p. 438 - 447
(2014/03/21)

σ-bond metathesis between M-X and RC(O)X′ (M = Pt, Pd; X, X′ = Cl, Br, I): Facile determination of the relative Δ G values of the oxidative additions of RC(O)X to an M(0) complex, evidence by density functional theory calculations, and synthetic applications
The novel utility of the ligand exchange reaction between M-X and RC(O)X′ (X, X′ = halogen; R = aryl, alkyl) is described. The relative ΔGs (ΔΔGs) of the oxidative additions of acid halides RC(O)X to M(PPh3)2Ln (M = Pt, Pd) were determined using the halogen-exchange reactions between X of trans-M(X)[C(O)R](PPh3)2 and X′ of RC(O)X′. Experimental thermodynamics data are reasonably consistent with those obtained by density functional theory (DFT) calculations. Activation parameters obtained by experiments as well as a systematic DFT study supported the fact that reactions occurred through slightly distorted quadrangular pentacoordinated σ-bond metatheses, in which the Cl atom underwent a more indirect course than the Br atom. Moreover, exchange reactions were employed as the accessible prototype for the conversion of halogen ligands of nickel triad complexes into heavier halogen ligands.
Kuniyasu, Hitoshi,Sanagawa, Atsushi,Nakane, Daisuke,Iwasaki, Takanori,Kambe, Nobuaki,Bobuatong, Karan,Lu, Yunpeng,Ehara, Masahiro
supporting information
p. 2026 - 2032
(2013/05/09)

Thioacids and thioacid salts for determining the enantiomeric excess of chiral compounds containing an electrophilic carbon center
The invention provides novel chiral compounds including 2-methoxy-2-trifluoromethylphenylacetic thioacid useful to react with and analyze other chiral compounds that have an electrophilic chiral carbon center.
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(2009/07/25)

Efficient carbonylation reactions in phosphonium salt ionic liquids: Anionic effects
(Formula Presented) Application of phosphonium salt ionic liquids in the carbonylation of aryl and vinyl halides is presented. Anionic effects were uncovered with the bromide ionic liquid emerging as the superior media. Acid bromide intermediates were detected in control experiments providing an extended view on the overall catalytic cycle involved. Solvent-free product isolation and recycling of the ionic liquid containing active Pd-catalyst are also demonstrated.
McNulty, James,Nair, Jerald J.,Robertson, Al
p. 4575 - 4578
(2008/03/12)

A mild and efficient reaction for conversion of carboxylic acids into acid bromides with ethyl tribromoacetate/triphenylphosphine under acid-free conditions
Acid bromides were prepared efficiently from carboxylic acids with readily available ethyl tribromoacetate and triphenylphosphine at room temperature under neutral conditions. The present process is applicable to the preparation of various acid bromides from aromatic and aliphatic carboxylic acids. Aromatic carboxylic acids were found to be more reactive than aliphatic carboxylic acids under reaction conditions.
Kang, Dong Ho,Joo, Tae Young,Lee, Eun Hwa,Chaysripongkul, Skaydaw,Chavasiri, Warinthorn,Jang, Doo Ok
p. 5693 - 5696
(2007/10/03)

Synthesis and utilization of functionalized polystyrene resins
Co-polymerised 4-bromopolystyrene has been converted to a range of polymer-supported reagents and scavengers by bromine-magnesium exchange using Oshima's trialkylmagnesate complex followed by quenching with a variety of electrophiles. Mitsunobu, halogenation and Wittig reactions, were explored to assess the utility of the resins for target oriented and diversity oriented synthesis.
Thomas, Gemma L.,B?hner, Christine,Ladlow, Mark,Spring, David R.
p. 12153 - 12159
(2007/10/03)

Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex as a reagent for preparation of carboxylic acid bromides
Triphenylphosphine-2,4,4,6-tetrabromo-2,5-cyclohexadienone complex was successfully used as a new reagent for the synthesis of carboxylic acid bromides which were isolated as individual substances or were identified by conversion into the corresponding anilides. The reaction is chemoselective, and it can be applied to polyfunctional compounds, e.g., hydroxy acids.
Matveeva,Podrugina,Sandakova,Zefirov
p. 1469 - 1472
(2007/10/03)

Fab I inhibitors
Compounds of the formula (I) are disclosed which are FabI inhibitors and are useful in the treatment bacterial infections: wherein: R1is H, C1-6alkyl or Ar—C0-6alkyl; R2is H, C1-6alkyl, Ar—C0-6alkyl, HO—(CH2)n— or R′OC(O)—(CH2)n—; R3is A—C0-4alkyl, A—C2-4alkenyl, A—C2-4alkynyl, A—C3-4oxoalkenyl, A—C3-4oxoalkynyl, A—C1-4aminoalkyl, A—C3-4aminoalkenyl, A—C3-4aminoalkynyl, optionally substituted by any accessible combination of one or more of R10or R7; R5is H, C1-6alkyl, Ar—C0-6alkyl or C3-6cycloalkyl-C0-6alkyl; A is H, C3-6cycloalkyl, Het or Ar; R7is —COR8, —COCR′2R9, —C(S)R8, —S(O)kOR′, —S(O)kNR′R″, —PO(OR′), —PO(OR′)2, —B(OR′)2, —NO2, or tetrazolyl; R8is —OR′, —NR′R″, —NR′SO2R′, —NR′OR′, or —OCR′2CO(O)R′; R9is —OR′, —CN, —S(O)rR′, —S(O)kNR′2, —C(O)R′, C(O)NR′2, or —CO2R′; R10is H, halo, —OR11, —CN, —NR′R11, —NO2, —CF3, CF3S(O)r—, —CO2R′, —CONR′2, A—C0-6alkyl-, A—C1-6oxoalkyl-, A—C2-6alkenyl-, A—C2-6alkynyl-, A—C0-6alkyloxy-, A—C0-6alkylamino- or A—C0-6alkyl —S(O)r—; R11is R′, —C(O)R′, —C(O)NR′2, —C(O)OR′, —S(O)kR′, or —S(O)kNR′2; R′ is H, C1-6alkyl, Ar—C0-6alkyl or C3-6cycloalkyl-C0-6alkyl; R″ is R′, —C(O)R′ or —C(O)OR′; R′″ is H, C1-6alkyl, Ar—C0-6alkyl, HO-(CH2)2—, R′C(O)—, (R′)2NC(O)CH2— or R′S(O)2—; X is H, C1-4alkyl, OR′, SR′, C1-4alkylsulfonyl, C1-4alkylsulfoxyl, —CN, N(R′)2, CH2N(R′)2, —NO2, —CF3, —CO2R′, —CON(R′)2, —COR′, —NR′C(O)R′, F, Cl, Br, I, or CF3S(O)r—; k is 1 or 2; m is 1, 2 or 3; n is 1 to 6; and r is 0, 1 or 2; or a pharmaceutically acceptable salt thereof.
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(2008/06/13)

COMPOUNDS USEFUL FOR INHIBITING CHK1
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(2008/06/13)

Spin selectivity in the oxygenation of singlet phenylhalocarbenes with oxygen
Singlet phenylhalocarbenes are shown to react with triplet oxygen and the apparent spin-forbidden oxygenation rates are strongly dependent on substituents, i.e. in the decreasing order of Br>Cl?F for halogen and of p-NO2>H?p-MeO for p-substituents. These results suggest the oxygenation of triplet halocarbene equilibrated with ground-state singlet, resulting in the first estimation of energy difference between the singlet and triplet states.
Makihara, Taiki,Nojima, Takayuki,Ishiguro, Katsuya,Sawaki, Yasuhiko
p. 865 - 868
(2007/10/03)

Trisubstituted carbocyclic cyclophilin binding compounds and their use
The present invention relates to novel, non-peptidic small organic compounds having an affinity for cyclophilin (CyP)-type immunophilin proteins, and to pharmaceutical compositions comprising one or more of the said compounds. The invention further relates to the uses of these compounds and compositions for binding CyP-type proteins, inhibiting their peptidyl-prolyl isomerase activity, and for research, development, and therapeutic applications in a variety of medical disorders.
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(2008/06/13)

Inhibitors of histone deacetylase
The invention relates to the inhibition of histone deacetylase. The invention provides compounds and methods for inhibiting histone deacetylase enzymatic activity. The invention also provides compositions and methods for treating cell proliferative diseases and conditions.
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(2008/06/13)

Probing the reactivity of photoinitiators for free radical polymerization: Time-resolved infrared spectroscopic study of benzoyl radicals
A series of substituted benzoyl radicals has been generated by laser flash photolysis of α-hydroxy ketones, α-amino ketones, and acyl and bis(acyl)phosphine oxides, all of which are used commercially as photoinitiators in free radical polymerizations. The benzoyl radicals have been studied by fast time-resolved infrared spectroscopy. The absolute rate constants for their reaction with n-butylacrylate, thiophenol, bromotrichloromethane and oxygen were measured in acetonitrile solution. The rate constants of benzoyl radical addition to n-butylacrylate range from 1.3 x 105 to 5.5 x 105 M-1 s-1 and are about 2 orders of magnitude lower than for the n-butylacrylate addition to the counterradicals that are produced by α-cleavage of the investigated ketones. Density functional theoretical calculations have been performed in order to rationalize the observed reactivities of the initiating radicals. Calculations of the phosphorus-centered radicals generated by photolysis of an acyl and bis(acyl)phosphine oxide suggest that P atom Mulliken spin populations are an indicator of the relative reactivities of the phosphorus-centered radicals. The α-cleavage of (2,4,6-trimethylbenzoyl)phosphine oxide was studied by picosecond pump-probe and nanosecond step-scan time-resolved infrared spectroscopy. The results support a mechanism in which the α-cleavage occurs from the triplet excited state that has a lifetime less than or equal to the singlet excited state.
Colley, Christopher S.,Grills, David C.,Besley, Nicholas A.,Jockusch, Steffen,Matousek, Pavel,Parker, Anthony W.,Towrie, Michael,Turro, Nicholas J.,Gill, Peter M. W.,George, Michael W.
p. 14952 - 14958
(2007/10/03)

Certain 5-alkyl-2-arylaminophenylacetic acids and derivatives
Disclosed are the compounds of formula I wherein R is methyl or ethyl; R1is chloro or fluoro; R2is hydrogen or fluoro; R3is hydrogen, fluoro, chloro, methyl, ethyl, methoxy, ethoxy or hydroxy; R4is hydrogen or fluoro; and R5is chloro, fluoro, trifluoromethyl or methyl; and pharmaceutically acceptable salts thereof, as selective COX-2 cyclooxygenase inhibitors; and pharmaceutically acceptable prodrug esters thereof.
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(2008/06/13)

COMBINATION PRODUCT AND METHODS OF USE
A pharmaceutical composition is disclosed which is comprised of an E-type prostaglandin ligand and a COX-2 selective inhibiting compound, in combination with a pharmaceutically acceptable carrier. Methods of treatment are also disclosed wherein an E-type prostaglandin ligand and a COX-2 selective inhibiting compound are adminstered in an amount that is effective to treat or prevent an E-type prostaglandin and/or COX-2 mediated disease or condition.
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(2008/06/13)

THE PREPARATION AND USE OF ORTHO-SULFONAMIDO ARYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE AND TACE INHIBITORS
The present invention relates to the discovery of novel, low molecular weight, non-peptide inhibitors of matrix metalloproteinases (e.g. gelatinases, stromelysins and collagenases) and TNF- alpha converting enzyme (TACE, tumor necrosis factor- alpha converting enzyme) which are useful for the treatment of diseases in which these enzymes are implicated such as arthritis, tumor growth and metastasis, angiogenesis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, proteinuria, aneurysmal aortic disease, degenerative cartilage loss following traumatic joint injury, demyelinating diseases of the nervous system, graft rejection, cachexia, anorexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease, HIV infection, age related macular degeneration, diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, ocular inflammation, keratoconus, Sjogren's syndrome, myopia, ocular tumors, ocular angiogenesis/neovascularization. The TACE and MMP inhibiting ortho-sulfonamido aryl hydroxamic acids of the present invention are represented by formula (I) where the hydroxamic acid moiety and the sulfonamido moiety are bonded to adjacent carbons on group A where: A is phenyl or naphthyl, optionally substituted by R, R, R and R; Z is aryl, heteroaryl, or heteroaryl fused to a phenyl, where aryl is phenyl or naphthyl optionally substituted by R, R, R and R; heteroaryl is a 5-6 membered heteroaromatic ring having from 1 to 3 heteroatoms independently selected from N, O and S, and optionally substituted by R, R, R and R; and when heteroaryl is fused to phenyl, either or both of the rings can be optionally substituted by R, R, R and R; and R, R, R, R, R, R, R, R and R are described in the specification, and the pharmaceutically acceptable salts thereof and the optical isomers and diastereomers thereof.
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(2008/06/13)

Acetylenic aryl sulfonamide and phosphinic acid amide hydroxamic acid TACE inhibitors
Hydroxamic acids having the formula are useful in treating disease conditions mediated by TNF-α, such as rheumatoid arthritis, osteoarthritis, sepsis, AIDS, ulcerative colitis, multiple sclerosis, Crohn's disease and degenerative cartilage loss.
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(2008/06/13)

Nitrogen-based halogenating agents and process for preparing halogen-containing compounds
Disclosed are a fluorinating agent represented by the general formula (1): wherein R1to R4are a substituted or unsubstituted, saturated or unsaturated alkyl group or a substituted or unsubstituted aryl group, and can be the same or different; R1and R2or R3and R4can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms; or R1and R3can bond to form a ring including a nitrogen atom or a nitrogen atom and other hetero atoms, for example: a preparation process of the fluorinating agent and a process for preparing fluorine compounds by reacting various compounds with the fluorinating agent. The invention has also disclosed that the fluorinating agent is very effective for fluorinating oxygen containing functional compounds.
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(2008/06/13)

PREPARATION AND USE OF ORTHO-SULFONAMIDO ARYL HYDROXAMIC ACIDS AS MATRIX METALLOPROTEINASE AND TACE INHIBITORS
The present invention relates to the discovery of novel, low molecular weight, non-peptide inhibitors of matrix metalloproteinases (e. g. gelatinases, stromelysins and collagenases) and TNF-α converting enzyme (TACE, tumor necrosis factor-α converting enzyme) which are useful for the treatment of diseases in which these enzymes are implicated such as arthritis, tumor growth and metastasis, angiogenesis, tissue ulceration, abnormal wound healing, periodontal disease, bone disease, proteinuria, aneurysmal aortic disease, degenerative cartilage loss following traumatic joint injury, demyelinating diseases of the nervous system, graft rejection, cachexia, anorexia, inflammation, fever, insulin resistance, septic shock, congestive heart failure, inflammatory disease of the central nervous system, inflammatory bowel disease, HIV infection, age related macular degeneration, diabetic retinopathy, proliferative vitreoretinopathy, retinopathy of prematurity, ocular inflammation, keratoconus, Sjogren's syndrome, myopia, ocular tumors, ocular angiogenesis/neovascularization. The TACE and MMP inhibiting ortho-sulfonamido aryl hydroxamic acids of the present invention are represented by the formula STR1 where the hydroxamic acid moiety and the sulfonamido moiety are bonded to adjacent carbons on group A.
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(2008/06/13)

Non-steroid progesterone receptor agonist and antagonist and compounds and methods
Non-steroidal compounds which are high affinity, high specificity ligands for progesterone receptors are disclosed. The compounds include synthetic derivatives of cyclocymopol and its diastereomers, spectroscopically and chromatographically pure (3R)-cyclocymopol monomethyl ether, which functions as a progesterone receptor antagonist, and spectroscopically and chromatographically pure (3S)-cyclocymopol monomethyl ether, which functions as a progesterone receptor agonist. Also disclosed are methods for employing the disclosed compounds for modulating processes mediated by progesterone receptors and for treating patients requiring progesterone receptor agonist or antagonist therapy.
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(2008/06/13)

Non-steroid androgen receptor antagonist compounds and methods
Non-steroidal compounds which are high affinity, high specificity ligand antagonists for the androgen receptor are disclosed. Also disclosed are methods for employing the disclosed compounds for modulating processes mediated by the androgen receptor and for treating patients requiring androgen receptor antagonist therapy.
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(2008/06/13)

FORMATION OF ACYL BROMIDES FROM CARBOXYLIC ACIDS AND N-BROMOSUCCINIMIDE; SOME REACTIONS OF BROMOCYANOTRIPHENYLPHOSPHORANE
Acyl halides, i.e., acyl bromides and acyl chlorides can be generated in high yields under mild conditions from the corresponding carboxylic acid in the presence of equivalent amounts of NBS/NCS and triphenylphosphine.The reaction between carboxylic acids, bromocyane and triphenylphosphine (Ph3PBrCN), affords under similar conditions acyl bromides.Bromocyanotriphenylphosphorane reacts also smoothly with epoxides, e.g., phenyloxirane. it appears, however, that the expected bromocyanides are not obtainable by this reaction, vicinal dibromides being formed instead.Key words: Acyl bromides, synthesis of from carboxylic acids and NBS, bromocyanotriphenylphosphorane, synthesis of alkylhalides.
Froeyen, Paul
p. 253 - 260
(2007/10/02)

Kinetic and Spectroscopic Studies on Acyl Radicals in Solution by Time-Resolved Infrared Spectroscopy
A number of acyl radicals, R=O, have been generated in hexane or di-t-butyl peroxide as solvent at room temperature by 308 nm laser flash photolysis, and their spectroscopic and kinetic properties have been examined by time-resolved infrared spectroscopy.The C=O stretching frequencies for the R=O radicals are found to be higher than those of the corresponding aldehydes, RCHO, by between 108 and 128 cm-1, an effect attributed to a higher C=O bond order in the radicals.For the R=O radicals some typical values of νC=O are: CH3=O, 1864 cm-1; (CH3)3C=O, 1848 cm-1; and C6H5=O, 1828 cm-1, while the corresponding acylperoxyl radicals, RC(O)OO, formed by reaction with oxygen have νC=O values of 1838, 1840 and 1820 cm-1, respectively.The acyl radicals exhibit a reactivity towards a variety of substrates that is roughly comparable to that of simple alkyl radicals.For reactions of the benzoyl radical some typical rate constants/M-1s-1 are: CCl4, 6.0*104; C6H5SH, 4.8*107; CCl3Br, 2.2*108; Tempo, 1.1+109; and oxygen, 1.8*109.Alkanoyl radicals have a rather similar reactivity to benzoyl.The propanoyl radical reacts with tributyltin deuteride with a rate constant of 3*105 M-1s-1.The hex-5-enoyl radical undergoes a 5-exo-trig cyclization to form the 2-oxocyclopentylmethyl radical with a rate constant of 2.2*105 s-1, a value which is almost identical to that for cyclization of the hex-5-enyl radical.It is hoped that our kinetic data will prove useful in the planning of organic synthetic strategies which involve acyl radical chemistry.
Brown, Carl E.,Neville, Anthony G.,Rayner, David M.,Ingold, Keith U.,Lusztyk, Janusz
p. 363 - 380
(2007/10/02)

Activated Basic Alumina Promotes a Mild, Clean and High-Yield Racemization-Free Synthesis of t-Butyl Esters from Chiral Acid Bromides and t-Butyl Alcohol
Esterification of a variety of acid bromides having even steric bulkiness with t-BuOH/activated basic alumina gave the corresponding t-butyl esters in good to excellent yields.In the case of chiral acid bromides, no racemization has been ascertained for the first time.
Nagasawa, Kazuo,Ohhashi, Keiko,Yamashita, Asami,Ito, Keiichi
p. 209 - 212
(2007/10/02)

Diarylstrylquinoline diacids and pharmaceutical compositions thereof
Compounds having the formula: STR1 are leukotriene antagonists and inhibitors of leukotriene biosynthesis. These compounds are useful as anti-asthmatic, anti-allergic, anti-inflammatory, and cytoprotective agents.
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(2008/06/13)

The conversion of carboxylic acids into acid bromides on BBr3-modified alumina
Carboxylic acids are converted into acid bromides on alumina which has been modified with boron tribromide. A different reaction occurs in solution.
Bains,Green,Tan,Pagni,Kabalka
p. 7475 - 7476
(2007/10/02)

First direct detection of transient organic free radicals in solution by time-resolved infrared spectroscopy. Kinetic studies on some acyl radicals
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Neville,Brown,Rayner,Lusztyk,Ingold
p. 1869 - 1870
(2007/10/02)

Radical mediated oxidations in organic chemistry. 3. An efficient and versatile transformation of aldehydes into amides
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Marko,Mekhalfia
p. 7237 - 7240
(2007/10/02)

Formation of carboxylic acid halides by the reactions of halogens with acetyl-, (phenylacetyl)-, and benzoylchlorobis(triphenylphosphine)platinum(II) and acetyl-, (phenylacetyl)-, and benzoylchloro(triphenylphosphine)palladium(II) complexes
The reactions of the acylmetal complexes trans-[M(PPh3)2Cl(RCO)] where M is Pt or Pd and R is CH3, C6H5CH2, or C6H5 with the halogens (X2) chlorine, bromine
Kubota, Mitsuru,Boegeman, Scott C.,Keil, Robert N.,Webb, Carl G.
p. 1616 - 1620
(2008/10/08)

DIBROMINATION OF BENZYLOXY-GROUPS: GLYCOSYL BROMIDES FROM BENZYL GLYCOSIDES
Bromination of benzyloxy groups in sugar derivatives with bromotrichloromethane and ultraviolet light rapidly gives α-bromobenzyloxy sugars.On further irradiation α,α-dibromobenzyloxy derivatives are formed from benzyl sugar ethers, whereas glycosyl bromides are produced from benzyl furanosides and pyranosides.
Collins, P. M.,Premaratne, P.,Manro, A.,Hussain, A.
p. 4721 - 4722
(2007/10/02)

Mechanistic Studies of the Palladium-Catalyzed Reaction of Methanol with Bromobenzene and CO To Produce Methyl Benzoate. 1. Stoichiometric Study
The mechanism of the palladium-catalyzed carbomethoxylation of bromobenzene to methyl benzoate in the presence of methanol and triethylamine has been investigated with Cylindrical Internal Reflectance Fourier Transform Infrared Spectroscopy (CIR-FTIR).The synthesis of the proposed catalytic intermediate Pd(Br)(C6H5)(P(C6H5)3)2 (1) was carried out, and the reaction of this species with CO to form Pd(Br)(COC6H5)(P(C6H5)3)2 (3) was confirmed.Both complexes were characterized by IR and 31P and 1H NMR spectroscopy.The stability of 3 in the absence of CO suggests that the carbonylation of 1 is irreversible; its stability in the presence of triethylamine establishes that reductive elimination of benzoyl bromide is not facile.In the absence of CO, the conversion of 3 to methyl benzoate was found to be rapid when both methanol and triethylamine were present, but very slow in the presence of methanol alone.A series of experiments in which 3 was allowed to react with methanol and a variety of amines in the absence of CO demonstrated a direct relationship between the rate of reaction and the amine basicity.These observations point to a mechanism in which methanol is initially deprotonated by the amine, and the methoxide ion thus produced attacks the benzoyl complex directly yielding methyl benzoate.When reaction of the benzoyl complex with methanol and triethylamine was carried out with bromobenzene also present, regeneration of 1 was observed via CIR-FTIR and confirmed by IR and proton NMR spectroscopy.The carbomethoxy species, Pd(Cl)(CO2CH3)(P(C6H5)3)2, was shown to be stable in the presence of bromobenzene, triethylamine, and methanol at 90 deg C, suggesting that this complex is not an active catalytic intermediate.These experiments substantiate the mechanism in Figure 8.
Moser, William R.,Wang, Andrew W.,Kildahl, Nicholas K.
p. 2816 - 2820
(2007/10/02)

Benzoin- und Benzilderivate als chemische Sensibilisatoren fuer die Tetrabromkohlenstoffspaltung
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Timpe, Hans-Joachim,Wagner, Roland,Paleta, Oldrich
p. 410 - 411
(2007/10/02)

Reaction of Hindered Trialkylsilyl Esters and Trialkylsilyl Ethers with Triphenylphosphine Dibromide: Preparation of Carboxylic Acid Bromides and Alkyl Bromides under MIld Neutral Conditions
A new route for a simultaneous deprotection-activation of hindered trialkylsilyl esters is described. tert-Butyldimethylsilyl, triisopropylsilyl, and tert-butyldiphenylsilyl carboxylates reacted with triphenylphosphine dibromide at room temperature in dichloromethane to give acid bromides in high yields.Reaction between hindered trialkylsilyl ethers and triphenylphosphine dibromide afforded alkyl bromides in excellent yields.The formation rate of acid bromides and alkyl bromides was increased when the reactions were carried out in the presence of a catalytic amount of ZnBr2.
Aizpurua, Jesus M.,Cossio, Fernando P.,Palomo, Claudio
p. 4941 - 4943
(2007/10/02)

ACYLATION AND BROMINATION OF SOME 2-MERCAPTOTHIENOPYRIMIDINONES AND SYNTHESIS OF THEIR 2-AMINO DERIVATIVES
The acylation of 2-thio-3-R-4-oxo-3,4-dihydrothieno-pyrimidines by means of benzoyl chloride was studied.Depending on the reaction conditions, it may take place with formation of S-substituted and N-substituted derivatives.The bromination of the sodium salts of thienopyrimidines and their S- and N-substituted derivatives is accompanied by the formation of disulfides, which do not react with electrophilic reagents but react with amines to give 2-amino derivatives of thienopyrimidines.
Khripak, S. M.,Yakubets, V. I.,Dobosh, A. A.
p. 1091 - 1094
(2007/10/02)

Halogen Mobility in SN2 Reactions of Carbonyl Compounds. Comparisons with Aromatic Halogen Mobility
Kinetic studies, using conductometric techniques, have been carried out for isopropanolysis (solvolysis) reactions of some alkanoyl, benzoyl and perfuoroalkanoyl halides, viz. butanoyl and benzoyl fluorides, chlorides,and bromides and perfluoropentanoyl fluoride and chloride.The halogen mobility orders, F N reactions at saturated and aromatic carbon, and have been discussed in mechanistic terms.The substrate class reactivity order is perfluoroalkanoyl >> benzoyl, alkanoyl.The actual ratios depend on which halogen is displaced, the ratios being larger on displacement of fluorine.
Miller, Joseph,Ying, Oi-Ling
p. 323 - 328
(2007/10/02)

Reagents and Synthetic Methods; 14. A Facile Synthesis of Carboxylic Acid Bromides and Esters under Neutral Conditions via Reaction of the Trimethylsilyl Esters with Triphenylphosphine Dibromide
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Aizpurua, Jesus Mari,Palomo, Claudio
p. 684 - 686
(2007/10/02)

Process for preparing amides by reaction in presence of molecular sieve
There is provided a process for preparing amides which comprises reacting an amine, or an amide, and an acid halide, or anhydride, in suitable molecular proportions, in an inert organic diluent, in the presence of an effective amount of a molecular sieve, until the reaction is completed, separating the molecular sieve, and recovering the amide from the organic mother liquor.
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(2008/06/13)

Reaction of Thionyl Bromide with Aromatic Aldehydes
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Saraf, S. D.
p. 673 - 676
(2007/10/02)

Element-organische Verbindungen; 9. Mitteilung. Synthese von Carbonsaeure-bromiden und Carbonsaeure-iodiden mit Hilfe von Halogentrimethylsilanen
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Schmidt, Arthur H.,Russ, Manuel,Grosse, Detlef
p. 216 - 218
(2007/10/02)

2-Acyl-3-substituted cyclopentan-1-ones and process for their preparation
1,3-Dicarbonyl compounds useful as medicines, agricultural chemicals, perfumes, and their intermediates are prepared by reacting a specific α,β-unsaturated carbonyl compound with a specific organic copper lithium compound in the presence of an aprotic inert organic solvent, and then reacting the reaction product with an organic carboxylic acid halide or anhydride. In particular, novel 2-acyl-3-substituted cyclopentan-1-ones and 2-acyl-3-substituted cyclohexan-1-ones having important physiological activities are provided.
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(2008/06/13)

Optical brightening agents of naphthalimide derivatives
A naphthalimide derivative having the formula STR1 wherein R is an alkyl, or cycloalkyl, an aralkyl, a haloalkyl, an alkoxyalkyl, a hydroxyalkyl, an N,N-dialkylaminoalkyl, an unsubstituted or halogen-, alkyl-, alkoxy- or hydroxy-substituted aryl, or an ammoniumalkyl; X is a group of the formula, STR2 wherein A is STR3 or an unsubstituted or halogen-substituted arylene, or a group of the formula, STR4 wherein R1 is hydrogen, an alkyl, phenyl, a hydroxyalkyl, or an alkoxyalkyl; Y is --CO--, --COO--, --CONR3 -- (where R3 is hydrogen or an alkyl), or --SO2 --; R2 is hydrogen, an alkyl, a cycloalkyl, an aralkyl, a haloalkyl, an alkyl- or aryl-substituted amino-alkyl, an unsubstituted or halogen-, alkyl-, alkoxy-, hydroxy-, amino- or alkylamino-substituted aryl, a group of the formula, STR5 (where R, R1 and Y are as defined above and R4 is a bivalent group), or a group of the formula, (where R5 is direct linkage or a bivalent group; Q+ is a substituted ammonium, a cycloammonium or a hydrazinium; and α- is an anion), Which is useful for optically brightening an organic polymer material.
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(2008/06/13)