- Synthesis of Arylstannanes via Palladium-Catalyzed Decarbonylative Coupling of Aroyl Fluorides
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Aryl stannanes are valuable precursors in organic transformations, but their synthetic methods are limited. Here we present a Pd-catalyzed decarbonylative stannylation of acid fluorides in the absence of exogenous base. Various aryl stannanes were efficiently prepared from bench-stable transition metal catalyst and ligand with broad functional group compatibility and substrate scope including natural products and pharmaceuticals. This protocol was also successfully used to a late-stage diversification of an existing uricosuric drug probenecid. (Figure presented.).
- Kayumov, Muzaffar,Zhao, Jian-Nan,Mirzaakhmedov, Sharafitdin,Wang, Dong-Yu,Zhang, Ao
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supporting information
p. 776 - 781
(2019/11/14)
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- Visible-Light-Driven Synthesis of Arylstannanes from Arylazo Sulfones
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The visible-light-driven preparation of (hetero)aryl stannanes was carried out under both photocatalyst- and metal-free conditions via irradiation of arylazo sulfones in the presence of hexaalkyldistannanes. The reaction shows a high efficiency and a wide substrates scope. The resulting crude organotin derivatives can be directly employed in a Stille protocol.
- Lian, Chang,Yue, Guanglu,Mao, Jinshan,Liu, Danyang,Ding, Yi,Liu, Zerong,Qiu, Di,Zhao, Xia,Lu, Kui,Fagnoni, Maurizio,Protti, Stefano
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supporting information
p. 5187 - 5191
(2019/07/03)
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- Synthesis of Aryl Trimethylstannane via BF3·OEt2-Mediated Cross-Coupling of Hexaalkyl Distannane Reagent with Aryl Triazene at Room Temperature
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BF3·OEt2-mediated cross-coupling of (SnMe3)2 with aryl triazene offers a new strategy for the synthesis of aryl stannane. A variety of synthetically useful aryl trimethylstannanes were produced in moderate to good yields with this metal-free approach. One-pot sequential Stille cross-coupling with different aryl bromides provides a short entry to both symmetrical and unsymmetrical biaryl compounds.
- Mao, Shuai,Chen, Zhengkai,Wang, Lu,Khadka, Daulat Bikram,Xin, Minhang,Li, Pengfei,Zhang, San-Qi
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p. 463 - 471
(2019/01/10)
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- Synthesis of arylstannanes by palladium-catalyzed desulfitative coupling reaction of sodium arylsulfinates with distannanes
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A novel Pd-catalyzed desulfitative cross-coupling reaction of sodium arylsulfinates with hexaalkyl distannanes is realized, allowing the facile synthesis of functionalized arylstannanes with moderate to excellent yields. The successful implement of gram-scale synthesis and tandem Stille coupling reaction demonstrates the potential applications of this method in organic synthesis.
- Lian, Chang,Yue, Guanglu,Zhang, Haonan,Wei, Liyan,Liu, Danyang,Liu, Sichen,Fang, Huayi,Qiu, Di
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supporting information
p. 4019 - 4023
(2018/10/04)
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- Synthesis of aryl trimethylstannanes from aryl halides: An efficient photochemical method
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An efficient transition-metal-free photochemical method featuring excellent functional group tolerance, mild reaction conditions and short reaction times has been discovered and developed for the synthesis of (hetero)aryl trimethylstannanes from (hetero)aryl halides. A photo-initiated radical chain mechanism was proposed based on preliminary mechanistic studies.
- Chen, Kai,He, Pei,Zhang, Shuai,Li, Pengfei
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supporting information
p. 9125 - 9128
(2016/07/21)
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- Synthesis of thiophene 1,1-dioxides and tuning their optoelectronic properties
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A 2,5-bis(tributylstannyl)thiophene 1,1-dioxide was prepared from 2,5-bis(trimethylsilyl)thiophene 1,1-dioxide, bis(tributyltin) oxide, and tetrabutylammonium fluoride (TBAF). The 2,5-bis(tributylstannyl)thiophene 1,1-dioxide and a 2,5-diiodothiophene 1,1
- Tsai, Chia-Hua,Chirdon, Danielle N.,Maurer, Andrew B.,Bernhard, Stefan,Noonan, Kevin J. T.
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supporting information
p. 5230 - 5233
(2013/11/06)
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- Synthesis of aryl trimethylstannanes from aryl amines: A sandmeyer-type stannylation reaction
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Sandmeyer-type stannylation: Stille coupling is one of the most powerful coupling reactions for C-C bond formation, whereas there are only limited methods to access aryl stannane compounds. A mild stannylation process based on a Sandmeyer-type transformation using aromatic amines as the starting materials is described. DCE: 1,2-dichloroethane. Copyright
- Qiu, Di,Meng, He,Jin, Liang,Wang, Shuai,Tang, Shengbo,Wang, Xi,Mo, Fanyang,Zhang, Yan,Wang, Jianbo
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supporting information
p. 11581 - 11584
(2013/11/06)
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- N-H and N=C bond formation via germanium(III) diradicaloid intermediates and C-S bond cleavage in reactions of the digermyne Ar'GeGeAr' (Ar' = C 6H3-2,6-(C6H3-2,6-Pr i2)2) with a
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Reactions of the digermyne Ar'GeGeAr' (Ar' = C6H3-2,6(C 6H3-2,6-Pr'2)2) (1) with four different azides R'N3 (R = Me3Sn, nBu3Sn, PhSCH 2, or 1-adamantanyl) a
- Wang, Xinping,Ni, Chengbao,Zhu, Zhongliang,Fettinger, James C.,Power, Philip P.
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p. 2464 - 2470
(2009/08/08)
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- Phenylboration of monoalkyn-1-yltin compounds
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The 1: 1 reactions of triphenylborane 1 with monoalkyn-1-yltin compounds Me3Sn-C≡C-R1 2 [R1 = 1Bu (a), Ph (b), ferrocenyl (c), Si(H)Me2 (d), SnMe3 (e)] afford mainly (> 80%) the corresponding alkene derivatives 3 by 1,1-phenylboration. Exchange B-Ph/Sn-C≡C-R1 takes place as a side reaction. The corresponding 1: 2 reaction with 2b leads to the dialkenylborane 4b (R 1 = Ph), of which the molecular structure could be determined by X-ray analysis. In contrast, the 1:2 reaction with 2e gave an aliene derivative 5e. The solution-state structures of compounds 3-5 have been confirmed by 1H, 11B, 13C and 119Sn NMR spectroscopy.
- Wrackmeyer, Bernd,Tok, Oleg L.,Milius, Wolfgang
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p. 1509 - 1513
(2008/10/09)
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- Metal cation-methyl interactions in CB11Me12 - salts of Me3Ge+, Me3Sn +, and Me3Pb+
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Oxidation of Me6M2 (M = Ge, Sn) and Me4Pb with the CB11Me12 radical in alkane solvents produced the insoluble salts Me3M+CB11 Me12, - characterized by CP-MAS NMR and EXAFS. The cations interact with methyl groups of CB11Me12- with coordination strength increasing from Pb to Ge. Density functional theory (DFT) calculations for the isolated ion pairs, Me3M+CB11Me 12- (M = Ge, Sn), revealed three isomers with the cation above methyl 2, 7, or 12, and not above a BB edge or a BBB triangle. The interaction has a considerable covalent component, with the cation attempting to perform a backside SE2 substitution on the methyl carbon. In a fourth less favorable isomer the cation is near methyl 1, inclined toward methyl 2, and interacts with hydrogens. DFT atomic charge distributions and plots of the electrostatic potential on the surface of spheres centered at the CB 11H12 and CB11Me12-, icosahedra display the effects of uneven charge distribution within the anion and contradict the common belief that the negative charge of the cage anion is concentrated primarily on the cage boron atoms 7-12; in CB11Me 12-, roughly half is on the cage carbon and the rest on methyls 7-12.
- Zharov, Ilya,Weng, Tsu-Chien,Orendt, Anita M.,Barich, Dewey H.,Penner-Hahn, James,Grant, David M.,Havlas, Zdenek,Michl, Josef
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p. 12033 - 12046
(2007/10/03)
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- Phenols as starting materials for the synthesis of arylstannanes via SRN11
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Phenols are converted into aryl diethyl phosphate esters (ArDEP), which on reaction with sodium trimethylstannide (1) or sodium triphenylstannide (2) in liquid ammonia afford arylstannanes by the SRN1 mechanism. Thus, the photostimulated reaction of phenylDEP (3), (4-methoxyphenyl)DEP (4), (4-biphenyl)DEP (5), (1-naphthyl)DEP (6), (2-naphthyl)DEP (7), and 2- (34), 3- (32), and (4-pyridyl)DEP (35) with 1 leads to monostannylated product in fair to excellent yields (20-98%). Also, substrates containing two or three leaving groups react with 1 under irradiation, affording the corresponding di- or tristannylated aryl compounds. With tetraethyl m-phenylene bisphosphate (15), tetraethyl p-phenylene bisphosphate (21), (4-chlorophenyl)DEP (22), and 1,3,5-tris(diethylphospho)benzene (30), the di- or trisubstitution products 1,3-bis(trimethylstannyl)benzene (19) (79%), 1,4-bis(trimethylstannyl)benzene (23) (95 and 97%), and 1,3,5-tris(trimethylstannyl)benzene (31) (57%) are obtained, respectively. Also, the reaction of 6 and 7 with 2 leads to substitution products in quantitative yields, and the reaction of 21, 22, and (4-bromophenyl)DEP (24) with 2 affords 1,4-bis(triphenylstannyl)benzene (38) in high yields (70-100%). On the other hand, the results obtained in the photostimulated reaction of 24 and (4-iodophenyl)DEP (25) with 1, as well as in the reaction of 25 with 2, clearly indicate a fast HME reaction.
- Chopa, Alicia B.,Lockhart, María T.,Dorn, Viviana B.
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p. 1425 - 1429
(2008/10/08)
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- Carbanions as intermediates in the formation of Grignard reagents
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The formation of reactive carbanions in Grignard reagents was discussed. Inter- and/or intramolecular migrations of organotin and organosilicon groups were also studied. Results showed that the high percentage of rearrangement reactions proves that the anionic species are not located on a minor pathway.
- Van Klink, Gerard P.M.,De Boer, Henricus J.R.,Schat, Gerrit,Akkerman, Otto S.,Bickelhaupt, Friedrich,Spek, Anthony L.
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p. 2119 - 2135
(2008/10/08)
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- Synthesis of arylstannanes from arylamines
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Arylamines have been converted into aryltrimethylammonium salts, which on reaction with sodium trimethylstannide (1) in liquid ammonia afford aryltrimethylstannanes by the SRN1 mechanism. With (4-methoxyphenyl)- (2), (1-naphthyl)- (4), phenyl- (6), (4-acetylphenyl)- (8), and (4-cyanophenyl)trimethylammonium salts (10) the substitution products are obtained in good to excellent yields (45-100%). Also, the photo-stimulated reaction of (2-pyridyl)trimethylammonium iodide (12) with 1 leads to the substitution product 13 (50%). With (4-chlorophenyl)trimethylammonium iodide (14) the disubstitution product 19 is obtained in 76% yield. On the other hand, the results obtained in the reaction of (4-bromophenyl)trimethylammonium iodide (15) with 1 clearly indicate a fast HME reaction in the dark. The ET process (SRN1) competes, although inefficiently, under irradiation.
- Chopa, Alicia B.,Lockhart, Maria T.,Silbestri, Gustavo
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p. 3358 - 3360
(2008/10/08)
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- Arylation of organotin halides with pentaarylantimony and pentaphenylbismuth
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Pentaarylantimony and pentaphenylbismuth arylate oranotin halides R3SnX and R2SnX2 (R = Alk, Ar; X = Cl, Br) in toluene at room temperature to aryltin derivatives R3SnAr and R2SnArX (initial reagent molar ratio 1:1) or R2SnAr2 (2:1) in 78-95% yield.
- Sharutin,Sharutina,Senchurin,Kovaleva,Shcherbakov,Gladyshev
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- Novel organoborane Lewis acids via selective boron-tin exchange processes - Steric constraints to electrophilic initiation by the boron halide
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With the purpose of preparing novel mono- and bidentate organoboron Lewis acids, the scope and limitations of synthesizing the requisite organoboranes by the boron-tin exchange between a boron halide and the appropriate organostannane have been examined in detail. The following organotin derivatives have been obtained either from the corresponding RMgBr or RLi reagent and MenSnCl4-n or from a Barbier procedure using the organic halide, Me3SnCl and magnesium metal: 1,2-bis(trimethylstannyl)ethyne, o-, m-, and p-bis(trimethylstannyl)benzenes, α,o-bis(trimethylstannyl)toluene, α,α-bis(trimethylstannyl)-o-xylene, and 2,2-dimethyl-2-stannaindane. The individual interaction of the 1,2-bis(trimethylstannyl)ethyne and the isomeric bis(trimethylstannyl)benzenes with Et2BBr produced the corresponding bis(diethylboryl)-derivatives. By contrast, with Et2BCl the α,o-bis(trimethylstannyl)toluene gave only o-diethylboryl-α-trimethylstannyltoluene and with BCl3 the α,α′-bis(trimethylstannyl)-o-xylene formed only α,α′-bis-(chlorodimethylstannyl)-o-xylene. Furthermore, in the attempted double boron-tin exchange between o-bis(trimethylstannyl)benzene and BCl3, an unprecedented rearrangement of the 1-(dichloroboryl)-2-(trimethylstannyl)benzene intermediate into its 1-[chloro(methyl)boryl]-2-(chlorodimethylstannyl) isomer was observed. Likewise, o-bis(trimethylstannyl)benzene with PhBCl2 produced by a similar rearrangement 1-[methyl(phenyl)boryl]-2-(chloro-dimethylstannyl)benzene. The thermolysis of such boranes led variously to definite dimers or ill-defined oligomers. Preliminary studies of the properties of these organoboranes have identified the heightened Lewis acidity of 1,2-bis(diethylboryl)ethyne and the π-electron delocalization involving the 2pΖ-boron orbitals in the 9,10-dihydro-9,10-diboraanthracene system. Finally, an electronic mechanism for the boron-tin exchange has been developed to account for the selectivity of the boron halide's attack at unsaturated carbon-tin bonds.
- Eisch, John J.,Kotowicz, Boguslaw W.
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p. 761 - 769
(2007/10/03)
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- Formation of 1,3,5-trilithiobenzene and its conversion to the corresponding magnesium, mercury, and tin derivatives
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Whereas the halogen-metal exchange approach from 1,3,5-tribromobenzene (3) to 1,3,5-trilithiobenzene (1) was unsuccessful, 1 was synthesized in high yield (about 80%) by reaction of 3 with LiDBB (lithium 4,4′-di-tert-butylbiphenyl). Compound 1 was used as
- Rot, Nicolette,Bickelhaupt, Friedrich
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p. 5027 - 5031
(2008/10/08)
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- Synthesis of asymmetrical aryl-tin compounds by cleavage of alkyl-tin bonds with sodium metal in liquid ammonia followed by SRN1 reactions with chloroarenes
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One methyl-tin bond was selectively cleaved from aryltrimethyltin compounds by sodium metal in liquid ammonia. The triorganylstannyl anions thus obtained are arylated by chloroarenes by means of photostimulated SRN1 reactions. Such reactions ca
- Yammal, Carlos C.,Podesta, Julio C.,Rossi, Roberto A.
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- Unsymmetrical Organotin Compounds in the Synthesis of Lanthanide Derivatives
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Transmetalation of lanthanide salts and Grignard-like organic lanthanide derivatives with mixed alkyl(vinyl)-aromatic organotin compounds was studied, and the possibility of synthesizing organolanthanide compounds through organotin derivatives was shown. The method is especiallly suitable for preparation of derivatives containing unsaturated groups.
- Rybakova,Starostina,Syutkina,Petrov
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p. 575 - 577
(2007/10/03)
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- Unusual metalation and halogen-metal exchange reactions between 1,3-xylyl crown ethers and organomagnesium reagents. X-ray structure of 2-[(p-tert-butylphenyl)magnesio]-1,3-xylylene-18-crown-5
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The scope of the surprising exchange reactions between 1,3-xylyl crown ethers and organomagnesium reagents was investigated. Halogen-metal exchange was found for both 2-bromo-1,3-xylylene-15-crown-4 (4) and 2-bromo-1,3-xylylene-18-crown-5 (14) as substrates, while metalation occurred with 1,3-xylylene-15-crown-4 (1). Attempts with other substrates failed, which demonstrates the highly specific structural requirements of these reactions. They are proposed to proceed after initial formation of a 1:1 complex of crown ether and organometallic reagent. Support was obtained by the metalation of 5-bromo-1,3-xylylene-15-crown-4 (17) at the intraannular 2-position. Product formation was investigated by 1H NMR spectroscopy and by derivatization. An X-ray structure determination of the metalation product 2-[(p-tert-butylphenyl)magnesio]-1,3-xylylene-18-crown-5 (25) was carried out: space group P1? (triclinic), a = 10.297 (1) ?, b = 10.825 (1) ?, c = 12.476 (2) ?, α = 109.27 (1)°, β = 94.43 (1)°, γ = 106.74 (1)°, V = 1234.0 (3) ?3, Z = 2, R = 0.052. Reactions of 2-(phenylmagnesio)-1,3-xylylene-15-crown-4 (2) with 9-phenylfluorene or with diphenylzinc suggest the formation of a stable organomagnesium cation of the type RMg+ (32, 33, 34; R = 1,3-xylylene-15-crown-4-2-yl). Metal-halogen exchange is not restricted to organomagnesiums as illustrated by the reaction of diphenylcalcium with 14, which gave 2-(phenylcalcio)-1,3-xylylene-18-crown-5 (35).
- Markies, Peter R.,Nomoto, Tateo,Schat, Gerrit,Akkerman, Otto S.,Bickelhaupt, Friedrich,Smeets, Wilberth J. J.,Spek, Anthony L.
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p. 3826 - 3837
(2008/10/08)
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- A multinuclear NMR study of asymmetrically coordinated η3-allyls in [PtCl(η3-allyl)(phosphine)] and [Pt(phenyl)(η3-allyl)(phosphine)] complexes
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The title complexes were prepared and fully characterized by multinuclear (1H, 31P, 13C, 195Pt) NMR methods. The 1H NMR resonances of the allyl groups were unequivocally assigned by using a combination of one- and two-dimensional NMR spectroscopic techniques. The spectroscopic data have been interpreted in terms of contributions of asymmetric η1-η2-allyl bonding modes to the more familiar symmetrical η3-allyl arrangement. The relative orientation and extent of the asymmetric η1-η2-bonding were shown to be markedly dependent upon the nature of the other ligands coordinated to platinum. On prolonged standing in chloroform solution, the title complexes rearranged to give the known complexes [X(R3P)Pt(μ-Cl)]2 and trans-XClPt(PR3)2 (X = Cl, Ph). Conversion of the allyl moiety to propene gas was shown by 1H NMR and gas chromatographic analysis.
- Clark, Howard C.,Hampden-Smith, Mark J.,Ruegger, Heinz
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p. 2085 - 2093
(2008/10/08)
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- Reactions of Trialkylstannane Anions R3Sn- with Arylstannanes ArSnR'3
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The reactions of trialkylstannane anions R3Sn- with arylstannanes ArSnR'3 have been investigated; trialkylstannane anions with arylstannanes at 50 deg C gave substitution products ArSnR3 in good yields.Most of these substitution products are diverted to r
- Mochida, Kunio
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p. 3299 - 3306
(2007/10/02)
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- SYNTHESIS AND SPECTROSCOPIC CHARACTERISTICS OF ARYLTRIMETHYL-SILICON, -GERMANIUM, AND -TIN COMPOUNDS
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The synthesis and spectroscopic characteristics of 28 para-substituted aryltrimethyl-silicon, -germanium, and -tin compounds are described.The infrared spectra show characteristic bands at 1245-1165 (methyl bend), 840-765 (methyl rock), and 1105-1020 (in-plane aromatic H bend) cm-1; the frequency of the last band was found to depend on the sum of the aromatic substituent masses, the presence or absence of metallic constituents in the substituent having little influence.The mass spectral fragmentation patterns are interpreted in terms of localization of positive charge on the metal atom, with subsequent bond cleavage behavior which obeys the rules for mass spectra of carbon compounds.
- Moerlein, S. M.
-
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- The Reaction of Calcium Atoms with Group 4B Catenates, Me3E-E'Me2R (E, E'=Si, Ge, Sn; R=Me, Cl)
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Calcium atoms are thought to be inserted into E-E' bonds of group 4B catenates, Me3E-E'Me2R (E, E'=Si, Ge, Sn; R=Me, Cl) to give the corresponding Me3E-Ca-E'Me2R compounds.
- Mochida, Kunio,Yamanishi, Takayuki
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p. 3429 - 3430
(2007/10/02)
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- Electon-Transfer, Halogen-Metal Exchange and Direct Processes in Formal Nucleophilic Substitutions on Alkyl Halides by Trimethyltinsodium
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Formal nucleophilic substitutions have been studied by simple trapping techniques designed to separate and estimate contributions of reactions proceeding by way of free radicals, by way of anions, and by way of geminate or synchronous processes.Reactions of trimethyltinsodium with organic halides in tetrahydrofuran at 0 deg C were examined, using dicyclohexylphosphine for trapping free radicals and tert-butylamine for free anionoids.Among 22 halides included in this study nine have been shown to involve two or all three of the mechanistic pathways.Primary chlorides reacted predominantly by a direct mechanism (SN2, geminate reaction of intermediates, or multicenter process).Branching, as in isobutyl and neopentyl, led to contributions from electron-transfer (free radical) and halogen-metal exchange (anionoid) mechanisms.Secondary bromides reacted predominantly by the ET process (major) and HME (minor) while the relative contributions from these were reversed in importance with the iodides.Triethylcarbinyl chloride reacted exclusively by elimination while the bromide reacted by ET alone or in competition with elimination. 1- and 2-bromoadamantanes reacted by ET, and 1-chloroadamantane showed no reaction after 10 days at -4 deg C.
- Smith, Gary F.,Kuivila, Henry G.,Simon, Reyna,Sultan, Leslie
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p. 833 - 839
(2007/10/02)
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- ORGANOMETALLIC COMPOUNDS. LXXII. REACTIONS OF RACEMIC TETRAORGANOTIN COMPOUNDS WITH BUTYLLITHIUM AND WITH LITHIUM ALUMINUM HYDRIDE
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Racemic methylneophylphenyltrityltin (I) reacts with an excess of butyllithium to give dibutylmethylneophyltin (II) in high yield, whereas bifluorenyl-9-ylmethylneophylphenyltin is converted with an excess butyllithium into butylmethylneophylphenyltin (II
- Gielen, Marcel,Tondeur, Yves
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p. 371 - 376
(2007/10/02)
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- SYNTHESIS OF ORGANOTRIALKYLSTANNANES. THE REACTION BETWEEN ORGANIC HALIDES AND HEXAALKYLDISTANNANES IN THE PRESENCE OF PALLADIUM COMPLEXES
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The aryl halides YC6H4X (X=Br or I) have been shown to react with the distannanes (R3Sn)2 (R=n-Bu or Me) in toluene in the presence of or to give the compounds YC6H4SnR3 for (a) R=n-Bu, Y=H, p-OMe, o-Me, p-Me, m-Cl, p-Cl, m-CN, p-COCH3 and m-NO2, and (b) R=Me, Y=H, p-OMe, p-Me, p-CN, p-COCH3, m-NO2 and p-NO2.Benzyl halides YC6H4CH2X (X=Cl or Br) similarly give YC6H4CH2SnR3 for (a) R=n-Bu, Y=H, m-OMe, p-OMe, m-Cl, m-CN, and m-NO2, and (b) R=Me, Y=m-Cl, m-CN, p-CN and m-NO2.These reactions are of special value as preparative procedures in cases in which Grignard or organolithium reagents cannot be used.Allyl chloride and bromide were likewise shown to react with (n-Bu3Sn)2 to give CH2=CHCH2SnBu3, but n-BuCl and n-BuBr gave only a trace of n-Bu4Sn.The mixed dimetallo species n-Bu3SnSiMe3 was shown to react with aryl bromides YC6H4Br (X=H, p-OMe, p-Me, or p-Cl) to give the arylsilicon compounds YC6H4SiMe3, with no aryltin products.
- Azizian, Hormoz,Eaborn, Colin,Pidcock, Alan
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- Investigation of some tricarbonyl-metal complexes of tin-substituted ligands by nuclear magnetic resonance, infrared, laser-Raman, tin-119m M?ssbauer, and mass spectroscopies
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Several novel metal-carbonyl complexes of tin-containing arene ligands of the general formulas (CH3)nSn(C6H5) 4-n·mM(CO)3 (where n = 2 or 3, m = 1 or 2, and M = Cr or Mo), [(CH3)
- Poeth, Thomas P.,Harrison,Long II, Thomas Veach,Willeford, Bennett R.,Zuckerman
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p. 522 - 528
(2008/10/08)
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