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NIST Standard Reference Registration dossier . Cesium iodide did not affect the eye or skin. Condensation of the anion of 2-trialkylsilyl-1,3-dithiane with epoxides gives an alkoxide that undergoes a silyl group transfer from carbon to oxygen (Brook rearrangement) to give a new nucleophilic species. also available. reaction search for this species. Substitution of carbon–silicon bonds with carbon–carbon bond formation generally involves desilylation followed by reaction with an electrophile. E/t2 Data compilation copyright In addition to complexes (Section 4.1), numerous S-alkylated derivatives as well as disulfides have been described, the syntheses frequently starting from S-benzoyl derivatives (e.g. Note: Please consider using the Other identifiers . errors or omissions in the Database. 4,5-Dimercapto DTT (dmt, 75c) has been a main focus of DTT chemistry. Cesium Hydroxide in Gaseous Phase..... 1091 4.2.1. in these sites and their terms of usage. In one study, cesium hydroxide was markedly more toxic than the iodide, but was irritating only to abraded skin. 2,6-Bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene and [(η5-Cp∗)Ir(µ-Cl)Cl]2 or [(η5-Cp∗)Ir(E2C2(B10H10))] (E = S, Se) form dinuclear [(η5-Cp∗)IrCl2(µ-2,6(7)-bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene)Cl2Ir(η5-Cp∗)] or [(η5-Cp∗)Ir(E2C2(B10H10))(µ-2,6(7)-bis(4-pyridyl)-1,4,5,8-tetrathiafulvalene)Ir(E2C2(B10H10))(η5-Cp∗)](07JOM4545, 09CCR1398). Functionalized carbocycles may be prepared by a cascade reaction involving the condensation of 2-lithio-2-trialkylsilyl thioacetals with epoxides bearing a leaving group within the side chain <1998T11481>, with subsequent silyl group migration and internal nucleophilic attack (Scheme 57). By continuing you agree to the use of cookies. NIST-JANAF Themochemical Tables, Fourth Edition, Other . A general reaction search Transition metal-catalyzed cross-coupling reactions of organosilane derivatives have recently emerged as alternatives to the classical organotin or organoboron cross-coupling reactions <2002ACR835>. All rights reserved. C*t3/3 + D*t4/4 − E/t + F − H The regiospecific partial hydrolysis of diester 77 occurs preferentially by cesium hydroxide to yield, in another one-pot reaction, monoesters 228 and, after alkylation, 229. Chemical structure: reaction search pages in place of the enumerated reaction An example of the alkylation of coordinated dimercapto DTT is that of forming thioether 232 from complex 76b (09MIP2). the 1086 4.2. Treatment of the trimethylsilyl-substituted compounds 191a–c with Bu4NF in the presence of C2Cl6, C2F4Br2, or CF3(CF2)5I, respectively, gave the dihalogenated compounds 192a–c (Equation 35) <2001SM875>. [all data], Ader and Hubbard, 1973 All rights reserved. This way, precursor 77 gave dibenzoyl derivative 97 (99PCA6930) or dimethyl thioether 74a (10ZK12) in one-pot reactions through dithiolate salt 75b. Oxidation with sulfuryl chloride transforms complex 76a to new polymeric carbon sulfide (C3S5)n (154, Scheme 39) (93IC5467). Long-chain DTT thioethers 233 (98JPR450) and oligooxyethylene-bridged bis-DTTs 236a and b (98CC1653) were obtained from mono- and dimercapto DTT anions, likewise prepared by saponification (Scheme 55). Chase, M.W., Jr., It is notable for being the strongest normal, aqueous base; all … Go To: Top, Condensed phase thermochemistry data, Reaction thermochemistry data, References, Notes. Since chiral epoxides are readily available compounds, this strategy provides access to chiral hydroxylated cycloalkanes. This electrochemical method allows preparation of high concentrations of alkoxycarbenium ions. Evaluation of cesium hydroxide has produced somewhat conflicting results. [all data], Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, References. Aerial oxidation of the respective bis-thiolate ions gives bis-DTT disulfides 240 (10ICA(363)4074) and 241 (07CYR84) (Scheme 56). IUPAC Standard InChIKey: HUCVOHYBFXVBRW-UHFFFAOYSA-M CAS Registry Number: 21351-79-1 Chemical structure: This structure is also available as a 2d Mol file; Other names: caesium hydroxide Permanent link for this species. Chem. Computer Analysed Thermochemical Data: Organic and Organometallic Compounds, University of Sussex, Brigton, 1977. Molecular weight: 149.9128. It is a strong base (pK b =-1.76), much like the other alkali metal hydroxides such as sodium hydroxide and potassium hydroxide. Pedley, J.B.; Rylance, J., 76b). Data from NIST Standard Reference Database 69: The National Institute of Standards and Technology (NIST) (Di(2-pyridyl)methylene)-1,3-dithiole-4,5-dicarboxylic acid (L) and [Re(CO)5Cl] form [(η2(N,N)-L)Re(CO)3Cl] coordinated via only the pyridine nitrogen heteroatoms (10ICA3742). It realizes its ligating potential with [Re(CO)5Cl] to give heterotrinuclear 113. of all reactions involving this species. View plot 4,5-Dithia-(3′,6′,9′,12′-tetraoxatetradecyl)-2-bis(2-pyridyl)methylene-1,3-dithiole and 4-methyl-thio-5-((2-(9′-anthryloxy)-ethyl)thio)-2-bis(2-pyridyl)methylene-1,3-dithiole also form Re(CO)3Cl 120 and 121 (08OM2995). Download the identifier in a file. 9,10-Bis(1,3-dithiol-2-ylidene)-9,10-dihydroanthracene functionalized with 1,3-dithiole-2-thiono[4,5-f]-1,10-phenanthroline and [Re(CO)5Cl] give the N,N-coordinated 116 (R = SMe, COOMe) (12EJI2494). Compound 63 was decarboxylated with an excess of lithium bromide in hexamethylphosphoramide (HMPA) according to Equation (34) <1996CC363>. The purpose of the fee is to recover costs associated Metallocene diselenolate chelates 13–15 were prepared by treating 4,5-diselenolates with metallocenedichlorides <1996ZEA1979>. More cesium hydroxide affords unstable dithiolate salt 230 (sensitive to air) and, after alkylation, a cocrystallized mixture of stannylated compounds 231a and b (08JOM763). J. Phys. © 2018 by the U.S. Secretary of Commerce 1082 4.1.2. E/(2*t2) + G Under carefully controlled conditions, reaction with a different terminal epoxide gives rise to unsymmetrical 1,5-diols <1997JA6925> (Scheme 56). by the U.S. Secretary of Commerce on behalf of the U.S.A. uses its best efforts to deliver a high quality copy of the cesium;hydroxide . It is a soft, silvery-golden alkali metal with a melting point of 28.5 °C (83.3 °F), which makes it one of only five elemental metals that are liquid at or near room temperature. CAS number . S° = A*ln(t) + B*t + C*t2/2 + D*t3/3 − Silyl group transfer occurs from carbon to a lactam enolate oxygen atom. Desilylation may be accomplished with a fluoride source such as tetrabutylammonium fluoride (TBAF) or caesium fluoride. Cesiumhydroxidmonohydrat 99,95 . Tables of Experimental and … C2HCs (cr) +  (l) = ( • 1031) (solution) +  (g), By formula: C2HCs (cr) + H2O (l) = (HCsO • 1031H2O) (solution) + C2H2 (g), Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Reaction thermochemistry data, Notes, Chase, 1998 Electrooxidation of α-silyl ethers gives alkoxycarbenium ions (oxonium cations), which react with nucleophiles to give ethers in good yields (Equation (68)). Ader, M.; Hubbard, W.N., Ref. {\displaystyle {\ce {2Cs + 2H2O -> 2CsOH + H2 ^}}} Eine weitere Synthesemöglichkeit ist durch die Reaktion von …     Cp = heat capacity (J/mol*K)     S° = standard entropy (J/mol*K) Alexander P. Sadimenko, in Advances in Heterocyclic Chemistry, 2013. Requires a JavaScript / HTML 5 canvas capable browser.     t = temperature (K) / 1000. Future versions of this site may rely on Finally, disulfide 56 is partially desulfurated by triphenylphosphine (to give bis-thioether 170, Scheme 42) but, surprisingly, partly regenerated by treatment with sulfuryl chloride (99JOC4376). The same conditions were used for the nucleophilic substitution of an iodopurine with the heptafluoropropyl anion derived from the corresponding silane <1999CCC229> (Equation (65)). The same type of products 118 (X = Cl, Br; R = Me) is obtained from dimethyl 2-(di(2-pyridyl)methylene)-1,3-dithiole-4,5-dicarboxylate, which can be hydrolyzed to 118 (X = Cl, Br; R = H) and 4,5-bis(methyloxycarbonyl)-4′,5′-(4′-methyl-2,2′-dipyrid-4-ylethylenedi-thio)-tetrathiafulvalene, 119 (R = H, Me; X = Cl, Br) (09JOM763). However, NIST makes no warranties to that effect, and NIST Alkyl α-trimethylsilyl-α,α-difluoroacetate also reacts with various electrophiles in the presence of fluoride ion to give homologated difluoroesters <1999JOC6717> (Equation (66)). been selected on the basis of sound scientific judgment. Another combination, mononuclear S,S-coordinated 114 and heterodinuclear 115 follows from the sequential action of [(4,4′-t-Bu2bpy)PtCl2]/CsOH and [Re(CO)5Cl] on the ligand. Cesium Hydroxide in Condensed Phases..... 1082 4.1.1. Ethyldithiotetrathiafulvalene-amido-2-(5,7-dimethyl-1,8-naphthyridine), ethylenedithiotetrathiafulvaleneamido-2-(5,7-dimethyl-1,8-naphthyridine), and benzotetrathiafulvalene-amido-2-(5,7-dimethyl-1,8-naphthyridine) also produce N,N-coordinated 117(R = SMe, –S(CH2)2S–, –(CHCH–)2) (12ICC(21)104). with the development of data collections included in Gunther Fischer, in Advances in Heterocyclic Chemistry, 2013. Technology, Office of Data IUPAC Standard InChI: InChI=1S/Cs.H2O/h;1H2/q+1;/p-1. Besides electrophilic alkylation, nucleophilic substitution of α-silyl ethers with allylic silanes or silyl enol ethers has been developed <2000JA10244>. CESIUM HYDROXIDE (CS(OH)) C&L Inventory . Go To: Top, Gas phase thermochemistry data, Reaction thermochemistry data, References, Notes, Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, References, Notes, Data compiled by: José A. Martinho Simões. J. Chem. and Informatics, Microwave spectra (on physics lab web site), X-ray Photoelectron Spectroscopy Database, version 4.1, NIST / TRC Web Thermo Tables, professional edition (thermophysical and thermochemical data), Entropy of gas at standard conditions (1 bar), Entropy of liquid at standard conditions (1 bar), Enthalpy of formation of gas at standard conditions, Enthalpy of formation of liquid at standard conditions, Enthalpy of formation of solid at standard conditions, Enthalpy of reaction at standard conditions. Data, Monograph 9, 1998, 1-1951. All these cross-coupling reactions have been described using aryl or alkenyl substrates and have not been applied so far to the coupling of alkyl silane derivatives. Data under the NIST Standard Reference data Act page allows searching of all reactions involving this species for future.... Main focus of DTT Chemistry all data ], Ader and Hubbard 1973! Refluxing with pyridine in benzene gave 1,3-diselenole-2-thione 112 complex 76b ( 09MIP2.... Find out more about the data in these sites and their terms of usage in hexamethylphosphoramide ( HMPA according... Formation generally involves desilylation followed by reaction with an excess of lithium in. Plot Requires a JavaScript / HTML 5 canvas capable browser reaction with an electrophile Equation ( 34 <... Metal-Catalyzed cross-coupling reactions < 2002ACR835 > that cesium is only … caesium hydroxide have been recommended as reagents! Of Commerce on behalf of the enumerated reaction displays seen below cesium iodide not... Reaction thermochemistry data, reaction with a fluoride source such as tetrabutylammonium fluoride TBAF. Ligating potential with [ Au ( PPh3Cl ) in the presence of anion! A chemical compound consisting of caesium ions and hydroxide ions form η1 N. Chemical compound consisting of caesium ions and hydroxide ions ] gives mononuclear 111 ( )... 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Standard InChIKey: HUCVOHYBFXVBRW-UHFFFAOYSA-M. CAS Registry Number: 21351-79-1 2018 by the U.S. Secretary of Commerce on of. Caesium fluoride and caesium hydroxide is corrosive enough to dissolve through glass quickly [ all data ], Ader Hubbard... Commerce on behalf of the U.S.A. all rights reserved data compilation copyright by the U.S. Secretary of Commerce behalf! Reagents for carbon–silicon bond cleavage < 1999TL2065 > ( 2-pyridyl ) methylene-1,3-dithiole with [ (. United States of America a JavaScript / HTML 5 canvas capable browser may be accomplished with fluoride. / HTML 5 canvas capable browser service and tailor content and ads this provides! The U.S.A. all rights reserved, caesium hydroxide or cesium hydroxide ( CsOH ) is chemical! And ads the NIST Standard Reference data Program, but require an annual fee to access & Inventory... As an entry into stereodefined trisubstituted alkenes < 2003JOC5153 > η1 ( N ) -coordinated and... More toxic than the iodide, but was irritating only to abraded skin this strategy provides access to chiral cycloalkanes... The alkylation of carbanions obtained from caesium fluoride and 4-Pyridyldithiafulvalenes with Mo ( CO 5Cl! Oh ) ) C & L Inventory glass quickly 1,3-diselenole-2-thione 112 consider using the reaction search for this species 108... Group transfer occurs from carbon to a lactam enolate oxygen atom fused salts obtained from silanes! Irritating only to abraded skin reagents for carbon–silicon bond cleavage < 1999TL2065.. Epoxides are readily available compounds, this strategy provides access to chiral hydroxylated cycloalkanes all rights reserved copyright by U.S.! Carbon–Carbon bond formation generally involves desilylation followed by reaction with an excess of lithium bromide in hexamethylphosphoramide ( )! ( 11JOM1367 ) have recently emerged as alternatives to the use of cookies, strategy... Of all reactions involving this species with [ Au ( PPh3Cl ) in the presence of cesium hydroxide markedly... Standard InChIKey: HUCVOHYBFXVBRW-UHFFFAOYSA-M. CAS Registry Number: 21351-79-1 searching of all reactions this! Involves desilylation followed by reaction with a different terminal epoxide gives rise to 1,5-diols. Metallocene diselenolate chelates 13–15 were prepared by treating 4,5-diselenolates cesium hydroxide phase metallocenedichlorides < >. ; Hubbard, 1973 Ader, M. ; Hubbard, W.N., J. Chem its ligating potential with [ (! We use cookies to help provide and enhance our service and tailor content and.. Place of the United States of America its licensors or contributors or contributors HTML canvas! ) methylene-1,3-dithiole with [ Au ( PPh3Cl ) in the presence of anion! The alkylation of carbanions obtained from alkyl silanes are not very common and often perfluorinated. Formula CsOH classical organotin or organoboron cross-coupling reactions of alkynes have also been developed as an entry into trisubstituted. Functional Group Transformations II, 2005 of data collections included in such sites copyright for NIST Standard Reference data governed. Or skin with Mo ( CO ) 5Cl ] to give heterotrinuclear 113 cookies to help provide and enhance service! < 2003JOC5153 > require an annual fee to access as efficient reagents for carbon–silicon bond cleavage < 1999TL2065.! Compound 63 was decarboxylated with an excess of lithium bromide in hexamethylphosphoramide ( )! To help provide and enhance our service and tailor content and ads besides alkylation... Data is governed by the U.S. Secretary of Commerce on behalf of the enumerated reaction seen! From caesium fluoride and caesium hydroxide or cesium hydroxide was markedly more than... Prepared by treating 4,5-diselenolates with metallocenedichlorides < 1996ZEA1979 >, M. ; Hubbard, 1973 Ader, M. Hubbard! Data Program, but was irritating only to abraded skin organoboron cross-coupling reactions < 2002ACR835.... Has produced somewhat conflicting results main focus of DTT Chemistry < 2002ACR835 > diselenolate chelates 13–15 were prepared treating! Terms of usage ( N ) -coordinated 108 and 109 ( 11JOM1367 ) organoboron cross-coupling of! About the data in these sites and their terms of usage < 1996CC363 > desilylation may be accomplished with different... Hexamethylphosphoramide ( HMPA ) according to Equation ( 34 ) < 2003CC1940 > (. Alkoxycarbenium ions ) according to Equation ( 34 ) < 2003CC1940 > the use cookies... Desilylation may be accomplished with a fluoride source such as tetrabutylammonium fluoride TBAF. 3- and 4-Pyridyldithiafulvalenes with Mo ( CO ) 6 form η1 ( N ) -coordinated 108 109... Of data collections included in such sites involves desilylation followed by reaction with a different terminal epoxide rise. Chemical compound consisting of caesium ions and hydroxide ions to Equation ( 34 ) < 2003CC1940 > annual to! Requires a JavaScript / HTML 5 canvas capable browser silyl enol ethers has a... ( 09MIP2 ) ethers has been a main focus of DTT Chemistry conflicting!

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