Month: April 2022

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Synthesis of ferrocene derivatives by means of boron- and halogen-substituted ferrocenes》. Authors are Nesmeyanov, A. N.; Sazonova, V. A.; Drosd, V. N..The article about the compound:Bromoferrocenecas:1273-73-0,SMILESS:Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25).Application In Synthesis of Bromoferrocene. Through the article, more information about this compound (cas:1273-73-0) is conveyed.

[R = ferrocenyl throughout this abstract] A series of new haloferrocene derivatives was prepared from RB(OH)2 (I) derivatives via RLi. Ferrocenyloxy derivatives and their esters were also synthesized and investigated. B(OBu)3 (92 g.) in Et2O was treated at -78° slowly with stirring with RLi from 17.6 g. ferrocene and BuLi (from 39 g. BuCl and 7.6 g. Li) in about 240 cc. Et2O, the mixture stirred until warmed to room temperature, kept overnight, decomposed with 10% H2SO4, the Et2O layer extracted with 10% aqueous KOH (40 cc., twice 10 cc., and five times 40 cc.). The 1st extract acidified and filtered gave 2.90 g. ferrocenylene-1,1′-diboronic acid (II), decomposed at about 180°; the 4th-8th alkali extracts gave 6.06 g. I, yellow, m. 143-8° (sealed tube); the 2nd and 3rd extracts gave a mixture of I and II which washed with Et2O left 0.44 g. II; the Et2O solution evaporated gave 0.72 g. I. I and II refluxed with aqueous ZnCl2 gave ferrocene. I (0.16 g.) in 20 cc. H2O treated with 0.19 g. HgCl2 in aqueous Me2CO gave 0.22 g. RHgCl, m. 192-4° (decomposition) (xylene). Aqueous I refluxed a few min. with excess ammoniacal Ag2O solution and extracted with Et2O, the extract evaporated, and the residue treated with petr. ether left 0.25 g. R2, m. 230-2° (decomposition) (absolute EtOH); the petr. ether solution evaporated gave 0.15 g. ferrocene. I (1 g.) in 200 cc. H2O treated at 50-60° with 1.70 g. CuCl22H2O in 50 cc. H2O, kept 15 min., steam distilled, and the product isolated from the distillate with Et2O gave 0.76 g. RCl, m. 58-9° (MeOH). In the same manner were prepared the following compounds (% yield and m.p. given): RBr, 80, 32-3°; 1,1′-dichloroferrocene (III), 75, 75-7°; 1,1′-dibromoferrocene (IV), 76, 50-1°. II (3.1 g.), 7 cc. MeOH, 4.7 g. CuCl2.2H2O, 75 cc. H2O, and 60 cc. C6H6 refluxed 2.5 h., cooled, distilled, the C6H6 layer separated, the aqueous layer added to the insoluble precipitate, diluted with 70 cc. C6H6, processed again in the same manner, saturated with NaCl, extracted with Et2O, the combined Et2O and C6H6 solutions concentrated to 50 cc., extracted with 10% aqueous KOH, and the extract acidified with 10% H2SO4 yielded 1.56 g. 1′-chloro-1-ferrocenylboronic acid (V), m. 159-61° (aqueous EtOH). Aqueous V boiled with ZnCl2 gave RCl. II and CuBr2 yielded similarly the 1′-Br analog (VI) of V, softened at about 130°, resolidified, m. 155-7°. Aqueous VI refluxed with ZnBr2 gave RBr. V (0.27 g.) in 5 cc. EtOH and 50 cc. H2O treated with 0.28 g. HgCl2 in aqueous Me2CO, the mixture heated 5 min., and filtered yielded 1′-chloro-1-ferrocenylmercuric chloride (VII), m. 144.5-45° (Me2CO), which with Na2S2O3 yielded bis(1′-chloro-1-ferrocenyl)mercury (VIIa), m. 151-2° (xylene-hexane). VI (0.30 g.) and 0.36 g. HgBr2 gave similarly 0.46 g. 1′-Br analog (VIII) of VII, m. 146.5-47° (Me2CO), which with Na2S2O3 yielded the di-Br analog of VIIa, m. 135-6° (MeNO2). VIII in xylene heated gave RBr. VII (1 g.) in 10 cc. xylene treated with 3 g. iodine in 10 cc. hot xylene, the mixture cooled, filtered, the residue washed with EtOH, shaken with 45 g. Na2S2O3 in 200 cc. H2O and with Et2O, and the Et2O layer evaporated gave 0.49 g. 1-chloro-1′-iodoferrocene, m. 42-4° (MeOH). VIII (0.80 g.) in 10 cc. xylene with 3 g. iodine in 10 cc. xylene yielded similarly 0.44 g. 1-bromo-1′-iodoferrocene, m. 28-30° (MeOH). VI (1 g) and 1.7 g. CuCl2 in 120 cc. H2O treated with steam and the product isolated from the distillate with Et2O gave 0.60 g. III, m. 75-7° (EtOH). RBr (0.60 g.) and 1.5 g. Cu phthalimide heated 2 h. at 135-40°, extracted with Et2O, and the extract worked up gave 0.48 g. N-ferrocenylphthalimide (IX), red crystals, m. 156-7° (EtOH). RCl (0.30 g.) and 1.5 g. Cu phthalimide gave similarly 0.24 g. IX. IX (0.3 g.), 0.5 cc. N2H4.H2O, and 5 cc. EtOH refluxed 40 min., diluted with H2O, extracted with Et2O, the Et2O solution extracted with 10% H2SO4, and the acidic extract basified with 10% aqueous KOH yielded 0.15 g. RNH2, m. 153-5°; N-Ac derivative m. 169-71°. RBr (0.30 g.) and 2 g. CuCN heated 2 h. at 135-40° and the product isolated with Et2O gave 0.20 g. RCN, m. 105.5-6.5°, also obtained in 42% yield from RCl and CuCN in C5H5N during 3 h. at 140-5°. RCl (2.5 g.) and 7.5 g. Cu(OAc)2 in 300 cc. 50% EtOH refluxed 15-20 min., diluted with H2O, and the product isolated with Et2O gave 2.3 g. ROAc, m. 64.5-6.5° (aqueous EtOH). RBr (0.30 g.) and 1.0 g. Cu(OAc)2 in 30 cc. 50% EtOH gave similarly 0.25 g. ROAc. I (2.5 g.) in 250 cc. hot H2O treated with 4.35 g. Cu(OAc)2 in hot H2O, the mixture cooled after 10 min., extracted with Et2O, and the residue from the extract treated with petr. ether left 0.42 g. R2, m. 230-2° (decomposition) (EtOH); the petr. ether solution evaporated gave 1.56 g. ROAc, m. 64.5-66° (EtOH). I (0.5 g.) in 60 cc. H2O and 1.0 g. Cu(O2CEt)2 in 40 cc. H2O yielded 0.30 g. EtCO2R, m. 30-1° (EtOH), and 0.08 g. R2. PhMgBr from 0.7 g. PhBr and 0.14 g. Mg in 10 cc. absolute Et2O treated under N with cooling with 0.44 g. ROAc in 5 cc. Et2O, the mixture stirred 1 h. at room temperature, decomposed with aqueous NH4Cl, and the Et2O phase worked up gave 0.23 g. MePh2COH, m. 79-81° (petr. ether); the alk. extract of the Et2O phase treated with CO2 precipitated 0.22 g. ROH, m. 166-70° (under N)(H2O). ROAc (0.40 g.), 6 cc. 10% aqueous KOH, and 8 cc. EtOH refluxed 50 min., the EtOH evaporated, the residual dark brown solution filtered, diluted to 13 cc., and treated with CO2 gave 0.29 g. ROH. VI (2 g.) in hot H2O refluxed with 5.4 g. Cu(OAc)2, cooled, and the product isolated with Et2O yielded 1.62 g. 1,1′-ferrocenylene diacetate (X), m. 55-6° (hexane). V (0.83 g.) and 2.2 g. Cu(OAc)2 gave similarly 0.66 g. X. II (2 g.) in 400 cc. hot H2O and 5.8 g. Cu(OAc)2 heated 40 min. on the water bath and the product isolated with Et2O yielded 0.90 g. X, m. 55-5.5° (hexane). IV (0.3 g.) and 1 g. Cu(OAc)2 in 30 cc. 50% EtOH refluxed 1 h., diluted with H2O, extracted with Et2O, and the extract worked up gave 0.16 g. X, m. 55.5-56° (hexane). X heated 10 min. with 20% aqueous KOH on the water bath and treated with CO2 gave 1,1′-dihydroxyferrocene (XI), yellow air-sensitive crystals, which with BzCl and alkali gave the dibenzoate. XI (from 0.80 g. X) in dry Et2O treated 1.5 h. with a stream of air, washed, and evaporated yielded 60 mg. dimeric cyclopentadienone, b8 120°, m. 96-8°. The hydrolyzates from ROAc and X treated under N with alkali, BzCl, and PhSO2Cl yielded the following compounds (% yield and m.p. given): ROBz, 85, 108.5-9.5°; ROSO2Ph, 90, 90-90.5°; dibenzoate of XI, 68, 114-15°; dibenzenesulfonate of XI, 72, 119.5-20.5°. ROAc (0.3 g.) and 0.5 cc. Me2SO4 in 5 cc. MeOH treated with 1.25 cc. 50% aqueous KOH gave 90% ROMe, m. 39.5-40.5°. X (0.20 g.) in 20 cc. MeOH treated with 3 cc. Me2SO4 yielded 95% 1,1′-dimethoxyferrocene, m. 35-6° (hexane). ROH and XI in 10% aqueous KOH refluxed 3 h. under N with 100% excess ClCH2CO2H, acidified with 10% H2SO4, and the product isolated with Et2O yielded 82% ROCH2CO2H, m. 136-7.5°, and 76% O,O’-(1,1′-ferrocenylene)diglycolic acid, m. 168.5-9.5° (H2O). ROH (0.30 g.), 1.5 g. powd. K2CO3, and 0.55 cc. CH2:CHCH2Br in 7 cc. absolute Me2CO refluxed 2 h. with stirring under N, diluted with H2O, extracted with Et2O, and the extract worked up gave 0.30 g. ROCH2CH:CH2, m. 28-30° (MeOH), which heated under N at 215-20° gave ROH.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Zhestkov, V. P.; Mironov, A. F.; Rosynov, B. V.; Ustynyuk, L. A.; Myagkova, G. I.; Evstigneeva, R. P. researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).COA of Formula: C9H13NO2.They published the article 《Studies on the synthesis of porphyrin a. II. Synthesis of porphyrins with higher saturated and unsaturated acyl substituents》 about this compound( cas:2199-44-2 ) in Bioorganicheskaya Khimiya. Keywords: deuteroporphyrin IX; biladiene cyclization; pyrrole reacion tripyrrene. We’ll tell you more about this compound (cas:2199-44-2).

Deuteroporphyrins IX [I, R1 = Me2C:CH(CH2)2CMe:CH(CH2)2CMe:CHCH2, Me2CH(CH2)3CHMe(CH2)3CHMe(CH2)2, Me2CBrCHBr(CH2)2CBrMeCHBr(CH2)2CBrMeCHBrCH2] were obtained in 33-92% yields by cyclization of the corresponding biladienes II, prepared from a pyrrole derivative and a tripyrrene.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 2199-44-2, is researched, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2Journal, Journal of Heterocyclic Chemistry called Microwave-accelerated synthesis of benzyl 3,5-dimethyl-pyrrole-2-carboxylate, Author is Regourd, Jasmine; Comeau, Ian M.; Beshara, Cory S.; Thompson, Alison, the main research direction is ethyl pyrrolecarboxylate benzyl alc transesterification microwave irradiation; acetylpyrrolecarboxylate benzyl deacetylation microwave irradiation; pyrrolecarboxylate benzyl preparation.SDS of cas: 2199-44-2.

Benzyl 3,5-dimethyl-pyrrole-2-carboxylate (I), a very useful pyrrole in porphyrin and dipyrromethene synthesis, can be synthesized via the Knorr-type reaction, but in low yield. Alternative routes to I have been developed involving the trans-esterification of Et 3,5-dimethyl-pyrrole-2-carboxylate and the deacetylation of benzyl 4-acetyl-3,5-dimethyl-2-carboxylate, both precursors being easily obtained using the Knorr reaction. These traditional methods involve treatment of the known products with a strong basic solution or heating for extended periods which often lead to decomposition The use of microwave energy to promote these two reactions proves to be an extremely efficient way to obtain I quickly, in high yield, and in excellent purity with no need for recrystallization Of particular note is the use of catalytic sodium methoxide in benzyl alc., rather than stoichiometric amounts of sodium benzoxide, to effect benzylation.

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In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called The observation of ion-pairing effect based on substituent effect of ferrocene derivatives, published in 2015-11-15, which mentions a compound: 1273-73-0, Name is Bromoferrocene, Molecular C10BrFe, Category: thiazolidine.

The ion-pairing effect was studied based on the substituent effect of ferrocene (Fc) derivatives using cyclic voltammetry. The presence of ion-pairing strongly affected the electrochem. redox behavior in the organic solvent. The formal redox potential (E0′, the average of anodic and cathodic peak potential) shifted neg. with the increasing ion-pairing effect. That was because the formation of ion pair (Fc+·ClO-4) was beneficial to equilibrium shift from Fc to Fc+ in thermodn. Electron-donating and electron-withdrawing substituents of ferrocene derivatives were employed for a deep study of ion-pairing effect, resp. Both ion-pairing effect and electron-donating substituent effect facilitated the neg. shift of E0′ for ferrocene derivatives, showing the pos. cooperativity. While the electron-withdrawing substituent effect resulted in the pos. shift of E0′ for ferrocene derivatives and was unfavorable for the oxidation of Fc derivatives, reflecting the neg. cooperativity with ion-pairing effect. The reversal phenomenon of weak electron-withdrawing substituent was revealed when the ion-pairing effect was stronger than the electron-withdrawing substituent effect, indicating that the ion-pairing function has a significant effect on electrochem. behavior of ferrocene derivatives

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Application of 1273-73-0. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about 1-(1′-Bromoferrocenyl)silver. Author is Nesmeyanov, A. N.; Sazonova, N. S.; Sazonova, V. A.; Meskhi, L. M..

Treating 0.5 g 1-bromo-1′-ferroceneboronic acid with Ag2O from 0.5 g Ag NO3 in NH4OH and heating briefly gave 53% 1-(1′-bromoferrocenyl)-silver, decomposed 125-6°. This with concentrated HCl 10 min gave 70% bromoferrocene, while pyrolysis in xylene gave a Ag mirror and 60% bis(1′-bromoferrocenyl), m. 138-40°. Treated with HgBr2 in C6H6 the Ag salt gave 80% 1-(1′-bromoferrocenyl)-mercuric bromide, m. 143-5°. The Ag derivative and BiBr3 in C6H6 in 3-4 hrs gave bromoferrocene and 50% tris(1′-bromoferrocenyl)bismuth, m. 179.5-81°. This kept in concentrated HCl 0.5 hr, then treated with aqueous NH4OH to neutrality, then percolated with H2S, gave a precipitate which was used for estimation of Bi after washing and drying to constant weight

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Zhang, Y.; Wang, Z.; Yan, C.; Li, G.; Ma, J. researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Quality Control of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.They published the article 《Synthesis and self-assembly of a novel tetrapyrrole containing dipyrrin units linked at the 3,3′-positions》 about this compound( cas:2199-44-2 ) in Tetrahedron Letters. Keywords: dipyrrin tetrapyrrole preparation selfassembly; zinc tetrapyrrole complex preparation crystal structure; mol structure zinc tetrapyrrole complex. We’ll tell you more about this compound (cas:2199-44-2).

A novel ligand comprising two dipyrrin units linked by a CH2 spacer at the 3-position was synthesized and used to prepare a double-stranded helical assembly. Its structure was confirmed by x-ray anal. of its Zn complex. A new approach to 3,3′-linked dipyrromethanes with CH2 as the spacer is also reported.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1273-73-0, is researched, SMILESS is Br[C-]12[Fe+2]3456789([C-]%10C6=C7C8=C9%10)C1=C3C4=C25, Molecular C10BrFeJournal, International Journal of Chemical Kinetics called Kinetics of the thermal decomposition of ferrocenyl azide: character of ferrocenyl nitrene, Author is Steel, C.; Rosenblum, M.; Geyh, A. S., the main research direction is ferrocenyl azide thermal decomposition kinetics; nitrene ferrocenyl.Category: thiazolidine.

The Arrhenius parameters for the thermal decomposition of ferrocenyl azide in isooctane are A = (5.1 ± 1.4) × 1012 s-1 and Eact = 113.1 ± 0.9 (kJ mol-1) and the rate is relatively insensitive to solvent (isooctane, benzene, acetonitrile; 1:1.7:2.4). The results indicate a relatively nonpolar transition state which is considerably “”tighter”” than for a normal bond fission reaction. The Arrhenius parameters are comparable to those for aromatic azides and do not offer any support for anchimeric assistance by the iron atom. A kinetic scheme is presented which accounts for the observed products: nitrogen, ferrocene, aminoferrocene, azoferrocene, and insoluble material. Rates of hydrogen abstraction by the intermediate ferrocenyl nitrene from cyclohexane, benzene, and acetonitrile are used to show that the nitrene is nucleophilic.

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Zhang, Chun; Santiago, Celine B.; Kou, Lei; Sigman, Matthew S. researched the compound: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole( cas:1428537-19-2 ).Reference of (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole.They published the article 《Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems》 about this compound( cas:1428537-19-2 ) in Journal of the American Chemical Society. Keywords: arylboronic acid unsaturated carbonyl enantioselective regioselective arylation Heck; aryl unsaturated carbonyl stereoselective preparation. We’ll tell you more about this compound (cas:1428537-19-2).

A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional anal. tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.

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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Bromoferrocene, is researched, Molecular C10BrFe, CAS is 1273-73-0, about N,N’-Diferrocenyl-N-heterocyclic Carbenes and Their Derivatives, the main research direction is crystal structure ferrocenyl imidazolidine imidazolidinethione imidazolinium imidazolinethione silver imidazolinylidene; mol structure ferrocenyl imidazolidine imidazolidinethione imidazolinium imidazolinethione silver imidazolinylidene; silver ferrocenylimidazolinylidene complex preparation structure; imidazolinylidene ferrocenyl silver complex preparation structure; imidazolinium ferrocenyl preparation structure electrochem reaction; imidazolinylium ferrocenyl preparation structure electrochem reaction; imidazolidine ferrocenyl preparation structure electrochem reaction; imidazolidinethione preparation; imidazolinethione preparation structure electrochem; carbene nitrogen heterocyclic silver complex preparation structure; electrochem ferrocenyl imidazolidine imidazolidinethione imidazolinium imidazolinethione silver imidazolinylidene; ferrocenyl imidazolidine imidazolidinethione imidazolinium imidazolinethione imidazolium imidazolinylidene preparation structure.Application of 1273-73-0.

In continuation of the authors’ work on Wanzlick/Arduengo carbenes containing redox-active ferrocenyl substituents the synthesis of N,N’-diferrocenyl imidazol(in)ium salts as precursors of imidazol(in)-2-ylidenes is reported. The necessary starting material for this chem. is aminoferrocene, which was prepared by an improved and large-scale synthesis by the sequence solid lithioferrocene, iodoferrocene, N-ferrocenylphthalimide, aminoferrocene. The preparation of N,N’-diferrocenyl heterocycles involves condensation of aminoferrocene with glyoxal to afford N,N’-diferrocenyldiazabutadiene [Fc-DAB], reduction, condensation with formaldehyde, and oxidation with trityl salts to yield N,N’-diferrocenylimidazol(in)ium salts. In situ deprotonation and trapping with electrophiles yielded the expected metal complexes and derivatives in some cases [Ag+ or S8], but attempted reaction with other transition metals [e.g., Pd(II)] failed to give the corresponding complexes, due to (i) steric hindrance by the two N-ferrocenyl substituents, (ii) reduced acidity of the imidazol(in)ium precursors, and (iii) inaccessibility of the free carbenes. Spectroscopic [IR, Raman, UV-visible, MS, NMR (1H, 13C, 109Ag)], structural [x-ray], and electrochem. [CV] properties are reported and compared to those of other N-heterocyclic carbene derivatives

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The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-4-(tert-Butyl)-2-(5-(trifluoromethyl)pyridin-2-yl)-4,5-dihydrooxazole(SMILESS: FC(C1=CN=C(C2=N[C@H](C(C)(C)C)CO2)C=C1)(F)F,cas:1428537-19-2) is researched.Product Details of 2199-44-2. The article 《Alkenyl Carbonyl Derivatives in Enantioselective Redox Relay Heck Reactions: Accessing α,β-Unsaturated Systems》 in relation to this compound, is published in Journal of the American Chemical Society. Let’s take a look at the latest research on this compound (cas:1428537-19-2).

A highly enantioselective and site-selective Pd-catalyzed arylation of alkenes linked to carbonyl derivatives to yield α,β-unsaturated systems is reported. The high site selectivity is attributed to both a solvent effect and the polarized nature of the carbonyl group, both of which have been analyzed through multidimensional anal. tools. The reaction can be performed in an iterative fashion allowing for a diastereoselective installation of two aryl groups along an alkyl chain.

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