C-Stannane derivatives of carbohydrates

1979 ◽  
Vol 57 (1) ◽  
pp. 38-43 ◽  
Author(s):  
Laurance D. Hall ◽  
Paul R. Steiner ◽  
Diane C. Miller
Keyword(s):  
Nmr Spectroscopy ◽  
Stable Carbon ◽  
Derivatives Of ◽  
C Nmr

Triphenyltin lithium (1) was reacted separately with 1,2:3,5-di-O-methylene-6-O-tosyl-α-D-glucofuranose (2), with methyl 2,3-anhydro-4,6-O-benzylidene-α-D-allopyranoside (4), and with methyl 2,3-anhydro-4,6-O-benzylidene-α-D-mannopyranoside (6), to form in each case a sugar-stannane derivative having a stable carbon-tin bond. These products have been studied by 1H and 13C nmr spectroscopy.

Synthese von Derivaten des 1-Adamantylbenzols /Synthesis of Derivatives of 1-Adamantylbenzene

1979 ◽  
Vol 34 (9) ◽  
pp. 1286-1288 ◽  
Author(s):  
Jörn-Volker WeiB ◽  
Victor Wray ◽  
Reinhard Schmutzler
Keyword(s):  
Nmr Spectroscopy ◽  
Lewis Acid ◽  
Type Reaction ◽  
Benzene Toluene ◽  
Derivatives Of ◽  
C Nmr

Abstractp-Di(1-adamantyl)benzene (6a), a mixture of the m- and p-isomers of 1-adamantyl-toluene (6b), and p-(l-adamantyl)bromobenzene (6c) were obtained in a Friedel-Crafts type reaction from 1-adamantyl fluoride and benzene, toluene, bromobenzene, respectively, in the presence of the Lewis acid phenyltetrafluorophosphorane. Characterisation of the products -all previously described in the literature -was by analysis and 13C NMR spectroscopy.

9-Silyl(-Germyl,-Stannyl) Substituted Derivatives of 1-(9-Fluorenyl)- germatranes. Synthesis, Characterisation, and Crystal Structures

1998 ◽  
Vol 53 (11) ◽  
pp. 1247-1254 ◽  
Author(s):  
Galina S. Zaitseva ◽  
Sergey S. Karlov ◽  
Bettina A. Siggelkow ◽  
Evgeni V. Avtomonov ◽  
Andrei V. Churakov ◽  
...  
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Crystal Structures ◽  
Elemental Analyses ◽  
Derivatives Of ◽  
C Nmr

9-Trimethylsilyl- and 9-trimethylgermyl substituted derivatives of 1-(9-fluorenyl)germatranes C13H8(R)Ge(OCH2CH2)3N (1 - 3) (1: R = H; 2: R = Me3Si; 3: R = Me3Ge) were prepared by the reaction of 9-tribromogermyl derivatives of fluorene C13H8(R)GeBr3 (4 - 6) with N(CH2CH2OSnAlk3)3 (7: Alk = Et; 8: Alk = Bu). 1-(9-Trimethylstannyl- 9-fluorenyl)germatrane (14) was synthesised by the reaction o f the germatrane (1) with Me3SnNMe2 . Formulas and structures were established by elemental analyses, (1H, 13C) NMR spectroscopy and mass spectrometry; crystal structures of 2 and 14 are reported.

Synthesis, spectroscopic characterization, and structural studies of organogermanium tri- and monothiocarbonates. Crystal structures of Me2Ge[S2CSEt]2, Ph3Ge[SCO2Me], Ph3Ge[SCO2(i-Pr)], and Ph2Ge[SCO2Me]2

1998 ◽  
Vol 76 (3) ◽  
pp. 319-334 ◽  
Author(s):  
John E Drake ◽  
Jincai Yang
Keyword(s):  
Mass Spectrometry ◽  
Nmr Spectroscopy ◽  
Crystal Structures ◽  
Sodium Salt ◽  
Variable Temperature ◽  
Spectroscopic Characterization ◽  
Structural Studies ◽  
Cell Parameters ◽  
Derivatives Of ◽  
C Nmr

Two series of S-alkyl trithiocarbonate derivatives of imethylgermane, Me2Ge[S2CSR]2, and halodiphenylgermane, Ph2GeX[S2CSR], where R = Me, i-Pr, n-Pr, n-Bu and X = Cl, Br, and three series of O-alkyl monothiocarbonate derivatives of triphenylgermane, Ph3Ge[SCO2R], diphenylgermane, Ph2Ge[SCO2R], and trimethylgermane, me3Ge[SCO2R], where R = Me, i-Pr, and n-Pr, have been prepared in 73-92% yields by the reaction of the potassium or sodium salt of the appropriate tri- or monothiocarbonic acid with dichlorodimethyl-, chlorotriphenyl-, dichlorodiphenyl-, and chlorotrimethylgermane. The compounds were principally characterized by infrared, Raman, and 1H and 13C NMR spectroscopy, including some variable temperature studies, as well as by mass spectrometry. Me2Ge[S2CSEt]2, 1: P21/m (No. 11) with cell parameters a = 6.647(4) Å, b = 7.423(2) Å, c = 16.290(4) Å, β = 91.07(3)°, V = 803.6(4) Å3, Z = 2, R = 0.0484,Rw = 0.0485. Ph3Ge[SCO2Me],13: P1bar (No. 2) with cell parameters a = 9.970(4) Å, b = 10.660(3) Å, c = 9.853(2) Å, α = 101.78(2)°, β = 109.98(2)°, γ = 89.76(3)°, V = 961.0(5) Å3, Z = 2, R = 0.0534, Rw = 0.0451. Ph3Ge[SCO2(i-Pr)], 14: P 1bar (No. 2) with cell parameters a = 14.386(7) Å, b = 18.598(6) Å, c = 9.223(3) Å, α = 102.85(3)°, β = 94.58(3)°, γ = 108.13(3)°, V = 2256(1) Å3, Z = 2, R = 0.0545, Rw = 0.0552. Ph2Ge[SCO2Me]2, 16: Cc, (No. 9) with cell parameters a = 11.790(4) Å, b = 13.696(5) Å, c = 23.232(6) Å, β = 92.26(3)°, V = 3748(2) Å3, Z = 8, R = 0.0563, Rw = 0.0512. The immediate environment about Ge is that of tetrahedral but the orientations of the thiocarbonate groups display interesting features.Key words: structure, germanium, phenyl, methyl, thiocarbonates.

Enantioselective fluorescent sensors for chiral carboxylates based on BINOL — Synthesis and chiral recognition

2010 ◽  
Vol 88 (4) ◽  
pp. 367-374 ◽  
Author(s):  
Kuo-xi Xu ◽  
Yu-xia Wang ◽  
Shu-yan Jiao ◽  
Jin Zhao ◽  
Chao-jie Wang
Keyword(s):  
Nmr Spectroscopy ◽  
Chiral Recognition ◽  
Fluorescent Sensors ◽  
Enantioselective Recognition ◽  
H Nmr ◽  
Recognition Ability ◽  
Chiral Materials ◽  
Fluorescent Recognition ◽  
Derivatives Of ◽  
C Nmr

The four novel derivatives of 1,1′-bi-2-naphthol (BINOL) have been prepared, and the structures of these compounds have been characterized by IR, MS, 1H and 13C NMR spectroscopy, and elemental analysis. The enantioselective recognition of these receptors has been studied by fluorescence titration and 1H NMR spectroscopy. The receptors exhibited different chiral-recognition abilities towards some enantiomers of chiral materials and formed 1:1 complexes between host and guest. The receptors exhibit excellent enantioselective fluorescent-recognition ability towards the amino acid derivatives.

scholarly journals Selektive Metallierung von BicycIo[3.2.1]octa-2,6-dien, II Distannylierte Derivate und stannylierte tricyclische Sekundärprodukte / Selective Metalation of Bicyclo[3.2.1]octa-2,6-diene, II Distannylated Derivatives and Stannylated Tricyclic Secondary Products

1988 ◽  
Vol 43 (11) ◽  
pp. 1405-1415 ◽  
Author(s):  
N. Hertkorn ◽  
F. H. Köhler
Keyword(s):  
Nmr Spectroscopy ◽  
Low Temperature ◽  
Nmr Spectra ◽  
Considerable Change ◽  
Coupling Constants ◽  
Secondary Products ◽  
Starting Compound ◽  
Derivatives Of ◽  
C Nmr ◽  
Dibromo Derivative

Abstract Distannylated bicyclo[3.2.1]octa-2,6-diene (1) with (CH3)3 Sn groups in positions exo-4 and 7 (7a), endo-4 and 7 (7b), exo-4 and 6 (7c), and probably exo-4 and endo-4 (7d) are obtained when 1 is treated first with an excess of n-BuLi/t-BuOK in alkane and then with (CH3)3 SnCl. Byproducts are monostannylated derivatives of 1 and l,4-bis(trimethylstannyl)but-2-ene (3). The formation of 7a/b/c is best understood when the two possible bicyclo[3.2.1]octa-2,6-dienyl dianions are generated as intermediates. 3,exo-4-Bis(trimethylstannyl)bicyclo[3.2.1]octa-2,6-diene (7e) is ob-tained from the corresponding dibromo derivative of 1 and (CH3)3SnLi with 3-bromo-exo-4-trimethylstannylbicyclo[3.2.1]octa-2,6-diene (9) as an intermediate. The bicyclic stannyl com-pounds are susceptible to a 1,5-homopentadienyl shift of a (CH3)3Sn group at relatively low temperature when the starting compound has the stannyl group in position 4 of 1 and when positions 6 or 7 are unsubstituted. Tricyclo[3.2.1.02.7]oct-3-enes with (CH3)3Sn groups in positions exo-6 (5a), endo-6 (5b), 3 and exo-6 (10a), and 3 and endo-6 (10b) are thus obtained. On further heating, 10b gives l-trimethylstannyl-3-vinylbenzene (11). All compounds have been studied systematically by NMR spectroscopy including δ(119Sn), δ(13C), δ(1H), 4/5J(119/117Sn-119Sn), nJ(119/117Sn-13C) , nJ(119/117Sn-1H), 1J(13C-1H ) , and nJ(1H-1H ). Among all nuclei, 119Sn gives the most simple spectra. From the 13C NMR spectra a series of useful increments of (CH3)3Sn groups emerges. The most interesting coupling constants are 5J(119/117Sn-119Sn), for which a considerable change with the dihedral angle is established, and nJ(119/117Sn-13C). For n = 3 and 4 the latter are especially useful because their angular dependence leads to unambiguous signal assignments.

17-(O-(2-Carboxyethyl)oxime) Derivatives of Androstanes of 3-Hydroxy-5α-, -5β-, -5-ene and 3-Oxo-4-ene Series

1995 ◽  
Vol 60 (1) ◽  
pp. 137-149 ◽  
Author(s):  
Vladimír Pouzar ◽  
Ivan Černý
Keyword(s):  
Nmr Spectroscopy ◽  
Hydroxy Group ◽  
Alkyl Acrylate ◽  
Subsequent Hydrolysis ◽  
Jones Reagent ◽  
Oxime Derivatives ◽  
Derivatives Of ◽  
C Nmr

Androstane 17-(O-(2-carboxyethyl)oxime) derivatives were prepared either by the reaction of 17-keto derivatives with corresponding substituted hydroxylamine or by the addition of 17-oximino derivatives to the alkyl acrylate and subsequent hydrolysis. Oxidation of the hydroxy group in position 3 in derivatives of this type was performed either by the Oppenauer reaction, transforming 5-ene derivatives into 3-oxo-4-enes, or with Jones reagent in the case of saturated 5α- or 5β-derivatives. Configuration 17E in the whole series of oximes was confirmed by the 1H and 13C NMR spectroscopy.

3,4-Disubstituted derivatives of 1,2,5-thiadiazole 1,1-dioxide. Ethanol addition reactions and electroreduction of 3-methyl-4-phenyl and 3,4-dimethyl derivatives in acetonitrile and ethanol solvents

1996 ◽  
Vol 74 (8) ◽  
pp. 1564-1571 ◽  
Author(s):  
José Alberto Caram ◽  
María Virginia Mirífico ◽  
Silvia Lucía Aimone ◽  
Enrique Julio Vasini
Keyword(s):  
Nmr Spectroscopy ◽  
Addition Reaction ◽  
Uv Spectroscopy ◽  
Equilibrium Constants ◽  
Addition Reactions ◽  
Solvent Mixtures ◽  
Second Order Reaction ◽  
Ethanol Addition ◽  
Derivatives Of ◽  
C Nmr

3-Methyl-4-phenyl-1,2,5-thiadiazole 1,1-dioxide (TMP), as well as 3,4-dimethyl-1,2,5-thiadiazole 1,1-dioxide (TMM), react with ethanol (EtOH), which adds to one of their C = N double bonds. The equilibrium constants for the addition reaction are measured in mixed acetonitrile (ACN) – EtOH solvents by means of UV spectroscopy in the case of TMP, and by 13C NMR spectroscopy in the case of TMM, since TMM presents only terminal UV absorption. Both equilibrium constants are also estimated through cyclic voltammetry (CV) experiments. In the case of TMP, the ethanol molecule adds to the C = N bond located on the methyl-substituted side of the substrate, according to 13C NMR spectroscopy and CV results. The electroreduction characteristics of the substrates and their ethanol addition products are studied using CV techniques in ACN, EtOH, and CAN–EtOH solvent mixtures. The radical anion formed by the first electron transfer to TMM is unstable and decomposes rapidly while that corresponding to TMP undergoes a relatively slow homogeneous second-order reaction with the substrate (k = 3 × 102 M−1 s−1). The equilibrium constant for EtOH addition and the voltammetric properties of the substrates are compared with those of the previously studied 3,4-diphenyl derivative (TPP). Key words: electrochemistry, thiadiazoles, structure–reactivity relations, kinetics.

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