Some acid-catalysed reactions of indol-3-yl and indol-2-yl disubstituted methanols

2009 ◽  
Vol 74 (7-8) ◽  
pp. 1137-1150 ◽  
Author(s):  
Mardi Santoso ◽  
Naresh Kumar ◽  
David StClair Black
Keyword(s):  
Crystal Structure ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
X Ray ◽  
Toluenesulfonic Acid ◽  
Acid Catalysed Reactions

1-Substituted indol-3-yl and indol-2-yl disubstituted methanols do not undergo acid-catalysed trimerisation to yield indolocyclotriveratrylenes, unlike the related primary 1-substituted indol-3-yl- and -2-ylmethanols. The 1-substituted indol-3-ylmethanols 10 and 11 gave diindol-3-ylmethanes 12 and 13, respectively, on treatment with p-toluenesulfonic acid in dichloromethane. In contrast, the indol-2-ylmethanols 22 and 23 gave the reduced indolo[3,2-b]carbazoles 24 and 25, respectively, on treatment with boron trifluoride etherate in benzene. An X-ray crystal structure of compound 24 is described.

Synthesis and structure of a stegane from dimethylmatairesinol

1984 ◽  
Vol 37 (8) ◽  
pp. 1775 ◽  
Author(s):  
RC Cambie ◽  
GR Clark ◽  
PA Craw ◽  
PS Rutledge ◽  
PD Woodgate
Keyword(s):  
Trifluoroacetic Acid ◽  
Oxidative Coupling ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
High Yield ◽  
X Ray Diffraction ◽  
X Ray

Oxidative coupling of dimethylmatairesinol with thallium tristrifluoroacetate (prepared in situ from thallium(III) oxide and trifluoroacetic acid) and boron trifluoride etherate gives a high yield of an isostegane which has been isomerized thermally to a stegane. Stereochemical assignments have been confirmed by X-ray diffraction studies.

scholarly journals La-Faujasite zeolite activated with boron trifluoride: synthesis and application as solid acid catalyst for isobutane–isobutene alkylation

2021 ◽  
Author(s):  
David Bolonio ◽  
Yolanda Sánchez-Palencia ◽  
María-Jesús García-Martínez ◽  
Marcelo F. Ortega ◽  
José Eugenio Ortiz ◽  
...  
Keyword(s):  
Boron Trifluoride ◽  
Solid Acid Catalyst ◽  
Acid Catalyst ◽  
Boron Trifluoride Etherate ◽  
Acid Sites ◽  
Alkylation Reaction ◽  
X Ray Diffraction ◽  
X Ray ◽  
Fau Zeolite ◽  
Sodium Form

AbstractThe sodium form of Faujasite Y (Na-FAU) zeolite has been synthesized by the hydrothermal method, and it has been exchanged with ammonium sulphate and later with lanthanum (III) chloride solutions to obtain the La-FAU catalyst. The three zeolites Na-FAU, NH4+-FAU and La-FAU have been characterized by microcrystalline X-ray diffraction, X-ray fluorescence, surface area, pore volume and Brönsted acid sites. The La-FAU catalyst has been successfully activated with boron trifluoride etherate, and it has been tested in the alkylation reaction of isobutane with isobutene up to 112 h of time on stream, since the raw La-FAU catalyst showed a rapid deactivation.

scholarly journals SYNTHESIS AND REACTIONS OF 1-(4’-BROMOPHENACYL)-3-(4’-BROMO-PHENYL)-4,6-DIMETHOXYINDOLE

2010 ◽  
Vol 5 (2) ◽  
pp. 156-162
Author(s):  
Jumina Jumina
Keyword(s):  
Acetic Acid ◽  
Sodium Borohydride ◽  
Trifluoroacetic Acid ◽  
Boron Trifluoride ◽  
Polyphosphoric Acid ◽  
Glacial Acetic Acid ◽  
Boron Trifluoride Etherate ◽  
Phosphoryl Chloride ◽  
Acetyl Ester ◽  
Toluenesulfonic Acid

  1-Phenacyl-3-aryl-4,6-dimethoxyindoles 2b and 2c were obtained in good yields respectively through cyclization of N,N-diphenacylaniline 1b and 1c in trifluoroacetic acid. However, instead of giving pyrroloindole 3c, treatment of phenacylindole 2c with polyphosphoric acid afforded indolizine 5 in 42% yield. Phenacylindole 2c reacts with the Vilsmeier aroylation reagent consisted of a mixture of phosphoryl chloride and p-chloro-N,N-dimethylbenzamide to give 2-aroylindole 6 (32%) and pyrroloindole 7 (22%). When treated with sodium borohydride, phenacylindole 2c gave alcohol 8 in 83% yield. Nonetheless, treatment of alcohol 8 with either p-toluenesulfonic acid in glacial acetic acid or boron trifluoride etherate in benzene did not give the desired dihydropyrroloindole 12. Instead, the reactions afforded respectively acetyl ester 9 and indole 10 in 56% and 63% yield.   Keywords: phenacylindole, aroylindole, pyrroloindole, and indolizine.

scholarly journals A Novel Ring Enlargement of 2H-Azirine-3-methyl(phenyl)amines via Amidinium-Intermediates: A New Synthetic Approach to 2,3-Dihydro-1,3,3-trimethylindol-2-one

2002 ◽  
Vol 57 (4) ◽  
pp. 444-452 ◽  
Author(s):  
Maged K.G Mekhael ◽  
Richard J. Smith ◽  
Stefan Bienz ◽  
Anthony Linden ◽  
Heinz Heimgartner
Keyword(s):  
Crystal Structure ◽  
Acetic Anhydride ◽  
Sodium Azide ◽  
Boron Trifluoride ◽  
Molecular Structures ◽  
Synthetic Approach ◽  
Successive Treatment ◽  
X Ray ◽  
Ring Enlargement ◽  
Methyl Phenyl

2,2,N-Trimethyl-N-phenyl-2H-azirin-3-amine (1a) was prepared by successive treatment of 2,N-dimethyl-N-phenylpropanamide (18) with phosgene, triethylamine, and sodium azide. Reaction of 1a in THF solution with boron trifluoride gave 2-amino-1,3,3-trimethyl-3H-indolium tetrafluoroborate (19) in high yield.T he latter reacted with acetic anhydride in pyridine to give a mixture of N-(2,3-dihydro-1,3,3-trimethylindol-2-yliden)acetamide (22) and 2,3-dihydro- 1,3,3-trimethylindol-2-one (21).On hydrolysis with aqueous HCl, 22 was converted to 21.T he molecular structures of 19 and 22 were established by X-ray crystal structure determination.

Boron Trifluoride Catalyzed Rearrangements of Novel Epoxide Derivatives of Manool and Manoyl Oxide

1993 ◽  
Vol 46 (8) ◽  
pp. 1125 ◽  
Author(s):  
PK Grant ◽  
GP Lynch ◽  
J Simpson ◽  
G Wong
Keyword(s):  
Lewis Acid ◽  
Boron Trifluoride ◽  
Boron Trifluoride Etherate ◽  
X Ray ◽  
X Ray Crystallography ◽  
Intramolecular Rearrangements ◽  
Derivatives Of

The preparation of four epoxides (1)-(4) derived from manool [labda-8(17),14-dien-13-ol] and manoyl oxide (8,13-epoxylabdane) via diosphenols is reported. Lewis acid promoted intramolecular rearrangements of these were investigated. Reaction of epoxide (1) with boron trifluoride etherate resulted in the isolation of a novel dimer (44), the structure being elucidated by X-ray crystallography. However, epoxides (2)-(4) yielded monomeric rearrangement products.

(3-Iminio-1-propenyl)oxy-borates: New Acyclic Betaines from Enaminocarbonyl Compounds and Boron Trifluoride or Triphenylboron – Synthesis, Crystal Structure Analysis, and Quantum Chemical Calculations

2003 ◽  
Vol 58 (2-3) ◽  
pp. 217-225 ◽  
Author(s):  
Joachim Nikolai ◽  
Gerhard Taubmann ◽  
Gerhard Maas
Keyword(s):  
Crystal Structure ◽  
Gas Phase ◽  
Structure Analysis ◽  
Lewis Acids ◽  
Boron Trifluoride ◽  
Natural Bond Orbital ◽  
Nbo Analysis ◽  
Crystal Structure Analysis ◽  
Dft Methods ◽  
X Ray

Adducts of various acyclic enaminoketones and enaminoaldehydes with the Lewis acids boron trifluoride and triphenylboron were prepared. The adducts were characterized by NMR (1H, 13C, 11B) and IR spectroscopy, FAB-MS, and X-ray crystal structure analysis of the adducts of (E)-3- diethylamino-3-phenyl-2-propenal with BF3 (4a) and BPh3 (5a), respectively. The adduct formation occurs at the oxygen atom of the enaminocarbonyl compound and gives rise to a betainic structure with expressed equalization of the bond orders in the enaminocarbonyl moiety. The gas-phase structures of complexes 4a and 5a and of the corresponding free enaminoaldehyde were determined computationally by RHF and DFT methods, and a Natural Bond Orbital (NBO) analysis was undertaken.

A study on α-RuCl3 crystal structure by scanning tunneling microscopy

1989 ◽  
Vol 47 ◽  
pp. 30-31
Author(s):  
H.-J. Cantow ◽  
H. Hillebrecht ◽  
S. Magonov ◽  
H. W. Rotter ◽  
G. Thiele
Keyword(s):  
Crystal Structure ◽  
Density Distribution ◽  
Scanning Tunneling Microscopy ◽  
Electron Density ◽  
Structure Determination ◽  
Electron Density Distribution ◽  
Scanning Tunneling ◽  
Monoclinic Space Group ◽  
Tunneling Microscopy ◽  
X Ray

From X-ray analysis, the conclusions are drawn from averaged molecular informations. Thus, limitations are caused when analyzing systems whose symmetry is reduced due to interatomic interactions. In contrast, scanning tunneling microscopy (STM) directly images atomic scale surface electron density distribution, with a resolution up to fractions of Angstrom units. The crucial point is the correlation between the electron density distribution and the localization of individual atoms, which is reasonable in many cases. Thus, the use of STM images for crystal structure determination may be permitted. We tried to apply RuCl3 - a layered material with semiconductive properties - for such STM studies. From the X-ray analysis it has been assumed that α-form of this compound crystallizes in the monoclinic space group C2/m (AICI3 type). The chlorine atoms form an almost undistorted cubic closed package while Ru occupies 2/3 of the octahedral holes in every second layer building up a plane hexagon net (graphite net). Idealizing the arrangement of the chlorines a hexagonal symmetry would be expected. X-ray structure determination of isotypic compounds e.g. IrBr3 leads only to averaged positions of the metal atoms as there exist extended stacking faults of the metal layers.

X-ray Crystal Structure of ?9-THC-tosylate

Planta Medica ◽  
2008 ◽  
Vol 74 (03) ◽  
Author(s):  
W Gul ◽  
P Carvalho ◽  
D Slade ◽  
M Avery ◽  
JR Duchek ◽  
...  
Keyword(s):  
Crystal Structure ◽  
X Ray

Crystal structure of an inclusion complex between chiral monoaza-15-crown-5 and S(–)-1-phenyl-ethyl ammonium percholorate

2003 ◽  
Vol 218 (5) ◽  
Author(s):  
Süheyla Özbey ◽  
F. B. Kaynak ◽  
M. Toğrul ◽  
N. Demirel ◽  
H. Hoşgören
Keyword(s):  
Crystal Structure ◽  
Inclusion Complex ◽  
Single Crystal ◽  
X Ray Diffraction ◽  
Space Group ◽  
X Ray ◽  
New Type

AbstractA new type of inclusion complex, S(–)-1 phenyl ethyl ammonium percholorate complex of R-(–)-2-ethyl - N - benzyl - 4, 7, 10, 13 - tetraoxa -1- azacyclopentadecane, has been prepared and studied by NMR, IR and single crystal X-ray diffraction techniques. The compound crystallizes in space group

Single Crystal Growth of High-Pressure Phases of Ice and Salt Hydrate Far Below the Original Melting Point by Mixing Alcohol: Crystal Structure Determination of Magnesium Chloride Heptahydrate

2020 ◽  
Author(s):  
Keishiro Yamashita ◽  
Kazuki Komatsu ◽  
Hiroyuki Kagi
Keyword(s):  
Crystal Structure ◽  
High Pressure ◽  
Crystal Growth ◽  
Single Crystal ◽  
Room Temperature ◽  
Growth Technique ◽  
Salt Hydrate ◽  
X Ray

An crystal-growth technique for single crystal x-ray structure analysis of high-pressure forms of hydrogen-bonded crystals is proposed. We used alcohol mixture (methanol: ethanol = 4:1 in volumetric ratio), which is a widely used pressure transmitting medium, inhibiting the nucleation and growth of unwanted crystals. In this paper, two kinds of single crystals which have not been obtained using a conventional experimental technique were obtained using this technique: ice VI at 1.99 GPa and MgCl<sub>2</sub>·7H<sub>2</sub>O at 2.50 GPa at room temperature. Here we first report the crystal structure of MgCl2·7H2O. This technique simultaneously meets the requirement of hydrostaticity for high-pressure experiments and has feasibility for further in-situ measurements.

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