Synthesis of 5-n-alkylresorcinol dimethyl ethers and related compounds via substituted thiophens

1971 ◽  
Vol 24 (12) ◽  
pp. 2655 ◽  
Author(s):  
D Buddhasukh ◽  
JR Cannon ◽  
BW Metcalf ◽  
AJ Power
Keyword(s):  
Raney Nickel ◽  
Stannic Chloride ◽  
Electrophilic Attack ◽  
Related Compounds ◽  
By Products

5-n-Alkylresorcinol dimethyl ethers have been synthesized by desulphurization of 2-(3,5-dimethoxybenzyl)-5-n-alkylthiophens with Raney nickel. The method has been adapted to the preparation of 9-(3,6- dimethoxyphenyl)nonyl alcohol which has been converted into both (2)- and (E)-15-(3,5-dimethoxyphenyl)pentadec-5-ene. ��� Friedel-Crafts acylation of 2-(3,5-dimethoxybenzyl)thiophen with n- hexoyl chloride, or with n-decoyl chloride, in the presence of stannic chloride, yielded the expected 2-(3,6-dimethoxybenzyl)-5-n- acylthiophens, but by-products were formed as the result of competing electrophilic attack on the 3,5-dimethoxybenzyl moiety. The chief by- products, which arise by subsequent Bradsher cyclodehydration, have been formulated as 5,7-dimethoxy-4-n-alkylnaphtho[2,3-b]thiophens. ��� An attempt to synthesize 1,14-bis(3,5-dimethoxyphenyl)tetradecane from 2,2?,6?,2?-terthienyl by an adaptation of this method was unsuccessful.

Lignin and related compounds. I. A comparative study of catalysts for lignin hydrogenolysis

1969 ◽  
Vol 47 (5) ◽  
pp. 723-727 ◽  
Author(s):  
J. M. Pepper ◽  
Y. W. Lee
Keyword(s):  
Comparative Study ◽  
Raney Nickel ◽  
Lignin Degradation ◽  
Soluble Fraction ◽  
Degradation Products ◽  
Quantitative Estimation ◽  
Liquid Chromatographic Separation ◽  
Lignin Degradation Products ◽  
Liquid Chromatographic ◽  
Related Compounds

A detailed comparative study has been made of the effectiveness of various catalysts for the hydrogenolysis of spruce wood lignin. The catalysts studied were Raney nickel, 10% palladium–charcoal, 5% rhodium–charcoal, 5% rhodium–alumina, 5% ruthenium–charcoal, and 5% ruthenium–alumina. Lignin degradation products were obtained initially as a chloroform-soluble fraction which was then divided and studied as diethyl ether-soluble and -insoluble fractions. Gas–liquid chromatographic separation of the ether-soluble fraction made possible the characterization and quantitative estimation of many of the lower molecular weight lignin degradation products.The data indicate that rhodium, palladium, and a limited amount of Raney nickel produce similar results as do ruthenium and an excess of Raney nickel; however, with the latter catalysts the degradation is more severe. In particular, rhodium–charcoal and palladium–charcoal appear to offer interesting advantages as catalysts for lignin hydrogenolysis.

Synthetical applications of activated metal catalysts. XXV. The hydrogenolysis of some phenyl derivatives of silicon by Raney nickel

1966 ◽  
Vol 19 (10) ◽  
pp. 1897 ◽  
Author(s):  
WHF Sasse ◽  
KO Wade
Keyword(s):  
Raney Nickel ◽  
Silicon Atom ◽  
Atmospheric Pressure ◽  
Nickel Catalysts ◽  
Metal Catalysts ◽  
Derivatives Of ◽  
Related Compounds ◽  
Raney Cobalt

Tetraphenylsilane and 11 related compounds have been cleaved by treatment at atmospheric pressure with Raney nickel catalysts to give mixtures of benzene and cyclohexane. Yields exceeding 90% are obtained with degassed Raney nickel and silanes. Silanols and siloxanes are less readily spilt. The presence of methanol in the reaction mixtures retards the fission of silicon-phenyl bonds. Tetracyclo-hexylsilane, cyclohexyltrimethylsilane, and hexa(n-hexyl)disiloxane did not react detectably with Raney nickel. Raney cobalt had no effect on tetraphenylsilane. A mechanism for the new reaction is discussed which involves chemisorption via the silicon atom, ejection of a phenyl anion, and hydrogenolysis of the absorbed triphenylsilyl species.

Desulfuration of steroidal thians

1982 ◽  
Vol 47 (11) ◽  
pp. 3148-3159 ◽  
Author(s):  
Alexander Kasal
Keyword(s):  
Raney Nickel ◽  
Optimum Conditions ◽  
Unsaturated Esters ◽  
Aprotic Medium ◽  
Derivatives Of ◽  
By Products

The reaction of 4-thia-5-cholesten-3-one (X) with Raney nickel in protic medium affords alcohol III, while A-nor-5β-cholestan-3-one (XXIII), A-bisnor-2,5-secocholestane (XXXI) and the esters of the type XVIII are formed as by-products. When aprotic medium is used compounds XXIII and XXXI are the main products. During desulfuration with a less active Raney nickel the mentioned substances are accompanied by 5-unsaturated derivatives of the type I, XIV and XXIX. Optimum conditions for the preparation of either saturated alcohols of type III or of unsaturated esters of type XIV were found.

Tricyclic neuroleptics: Synthesis of metabolites of isofloxythepin and some related compounds

1990 ◽  
Vol 55 (9) ◽  
pp. 2282-2303 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Jílek ◽  
Josef Pomykáček ◽  
Vladimír Valenta ◽  
Marta Hrubantová ◽  
...  
Keyword(s):  
Formic Acid ◽  
Substitution Reaction ◽  
Lithium Aluminium Hydride ◽  
Enol Ether ◽  
Basic Product ◽  
Lithium Aluminium ◽  
Toluenesulfonic Acid ◽  
Neuroleptic Agent ◽  
Related Compounds ◽  
By Products

The isofloxythepin (I) metabolite IV was synthesized via the acids IX and XI and the esters X and XII. The enamine VIII was prepared from 3-fluoro-8-(2-propyl)dibenzo[b,f]thiepin-10(11H)-one by two methods and was reduced to I. Cloflumide (II) was obtained by reaction of 2,10-dichloro-7-fluoro-10,11-dihydrodibenzo[b,f]thiepin with 3-(1-piperazinyl)propionamide and was oxidized to the sulfoxide XVI. The unsaturated analogue XVII of clopithepin (III) was prepared from 2-chlorodibenzo[b,f]thiepin-10(11H)-one by reaction with 2-bromoethanol in the presence of 4-toluenesulfonic acid in boiling benzene and by the following substitution reaction with 2-(1-piperazinyl)ethanol. An improved synthesis of 6-methyldibenzo[b,f]thiepin-10(11H)-one (XIX) was elaborated. The acid XXVII was synthesized and cyclized with polyphosphate ester. A mixture of compounds was formed from which the ketone XXXVI was isolated and processed by reaction with formamide and formic acid at 200 °C. One of the products was characterized as the formamide XXXIII and was reduced with lithium aluminium hydride to a basic product supposed to be XXXIV. A series of by-products was isolated and characterized. The enamine VIII (V⁄FB-17 156) was found to be a strong neuroleptic agent, similar to isofloxythepin (I). The enol ether XVII (V⁄FB-17 733) was characterized as a mild, practically noncataleptic neuroleptic agent.

scholarly journals Behavior of Viscous Liquid Byproduct Formed in Exhaust Tube by Silicon Carbide Epitaxial Growth

2019 ◽  
Vol 8 (12) ◽  
pp. P805-P810
Author(s):  
Ichiro Mizushima ◽  
Hitoshi Habuka
Keyword(s):  
Silicon Carbide ◽  
Epitaxial Growth ◽  
Viscous Liquid ◽  
Growth Process ◽  
Room Temperature ◽  
Product Layer ◽  
Layer Formation ◽  
Low Concentrations ◽  
Related Compounds ◽  
By Products

The behavior of the by-product produced in an exhaust tube by the semiconductor silicon carbide epitaxial growth process was evaluated. The by-product layer was a dark-colored viscous liquid; it captured precursor gases and gaseous by-products, such as hydrogen, monosilane, propane, hydrogen chloride and chlorosilanes. These captured gases were spontaneously emitted in ambient nitrogen at room temperature. By an etching process using a chlorine trifluoride gas at low concentrations in ambient nitrogen, the by-product layer could be safely decomposed to gaseous fluorides of silicon and carbon. After finishing the etching, there remained a small amount of residue which included particles of carbon, silicon carbide and related compounds. Based on these results, the by-product layer formation process was discussed.

Chemical vapor deposition of copper via disproportionation of hexafluoroacetylacetonato(1,5 -cyclooctadiene)copper(I), (hfac)Cu(1,5-COD)

1992 ◽  
Vol 7 (2) ◽  
pp. 261-264 ◽  
Author(s):  
A. Jain ◽  
K.M. Chi ◽  
M.J. Hampden-Smith ◽  
T.T. Kodas ◽  
J.D. Farr ◽  
...  
Keyword(s):  
Chemical Vapor Deposition ◽  
Vapor Deposition ◽  
Electron Spectroscopy ◽  
Chemical Vapor ◽  
Copper Films ◽  
Temperature Range ◽  
Measured Activation Energy ◽  
Measured Activation ◽  
Related Compounds ◽  
By Products

Hot- and cold-wall chemical vapor deposition (CVD) using the volatile copper(I) compound (hfac)Cu(1,5-COD), where hfac = 1,1,1,5,5,5,-hexafluoroacetylacetonate and 1,5-COD = 1,5-cyclooctadiene, as a precursor was carried out in hot-wall and warm-wall, lamp-heated reactors using SiO2 substrates that had been patterned with Pt or W, over a temperature range 120 °C-250 °C. Deposition was observed onto Pt, W, and SiO2 over this temperature range at rates of up to 3750 Å/min to give copper films that contained no detectable impurities by Auger electron spectroscopy and gave resistivities of 1.9-5.7 μ ohm cm. The volatile by-products formed during deposition were 1,5-COD and Cu(hfac)2 and a mass balance was consistent with the quantitative disproportionation reaction: 2(hfac)Cu(1,5-COD) → Cu + Cu(hfac)2 + 2(1,5-COD). The measured activation energy for this CVD reaction was 26(2) kcal/mol. The absence of selectivity for metal surfaces in the presence of SiO2 is in contrast to CVD results for the related compounds (β-diketonate)Cu(PMe3) where β-diketonate = hfac, 1,1,1-trifluoroacetylacetonate (tfac), and acetylacetonate (acac).

Dibenzo[b,f]thiepin-10-carbonitrile, its 10,11-dihydro derivative, some transformation products and related compounds

1983 ◽  
Vol 48 (4) ◽  
pp. 1187-1211 ◽  
Author(s):  
Karel Šindelář ◽  
Jiří Holubek ◽  
Miroslav Ryska ◽  
Emil Svátek ◽  
Jiří Urban ◽  
...  
Keyword(s):  
Main Product ◽  
Cardiovascular Effects ◽  
Transformation Products ◽  
Anticonvulsant Effect ◽  
Cuprous Cyanide ◽  
High Doses ◽  
Hydrolysis Of ◽  
Related Compounds ◽  
By Products ◽  
Dichloro Derivative

Reactions of 10-bromodibenzo[b,f]thiepin (IIIa), its 2-chloro derivative IIIb and 2,8-dichloro derivative IIIc with cuprous cyanide in boiling dimethylformamide gave the carbonitriles Iabc out of which the first two were reduced with sodium borohydride to the 10,11-dihydro derivatives IVab; the amides VIIab were obtained as by-products. Alkaline hydrolysis of the nitriles IVab or their mixtures with the amides VIIab afforded the acids VIIIab. By the addition of 3-dimethylaminopropylmagnesium chloride to the nitrile Ia cis and trans-11-(3-dimethylaminopropyl)-10,11-dihydrodibenzo[b,f]thiepin-10-carbonitriles (XVIII) were obtained. Alkylation of the nitrile IVa with 2-dimethylaminoethyl chloride and 3-dimethylaminopropyl chloride resulted in the 10-(dimethylaminoalkyl) derivatives XX and XXI. A reaction of the crude cyano alcohol XXIII with phosphorus tribromide afforded the 2-bromoethyl derivative XXIV as a by-product only. The main product was the hydrobromide of the spirocyclic imidate XXX which affords by acid hydrolysis the spirocyclic lactone XXXI. An analogous sequence proceeding via the ether XXVI and the alcohol XXVII leads to the 10-(3-bromopropyl) derivative XXVIII as the main product. An attempt at preparing the same substance by alkylation of the nitrile IVa with 1,3-dibromopropane gave stereoisomeric dinitriles XXXII. At high doses the amides VIIab reveal an anticonvulsant effect, the acids VIIIab antiinflammatory actions, the basic nitrile cis-XVIII antireserpine activity and the basic nitriles XX and XXI a central depressant and pseudo-analgesic activity in addition to further peripheral and cardiovascular effects.

Synthetical applications of activated metal catalysts. XXVI. The formation of biaryls from azahydrocarbons under the influence of rhodium-on-carbon

1968 ◽  
Vol 21 (1) ◽  
pp. 207 ◽  
Author(s):  
JC Carey ◽  
WHF Sasse
Keyword(s):  
Raney Nickel ◽  
Metal Catalysts ◽  
Boiling Points ◽  
By Products

The action of degassed rhodium-on-carbon on 14 azahydrocarbons has been examined. 2,2'-Biaryls are formed in 15-50% yield from quinoline, 6-methyl-quinoline, 7-methylquinoline, 4-phenylpyridine, and 4-benzylpyridine at their boiling points, and from benzo[f]quinoline at 320-330�. By-products formed from quinoline include 2,3'-biquinolyl, two triquinolyls, and the products of hydrogenolysis previously obtained from experiments with quinoline and degassed Raney nickel. The methylquinolines undergo demethylation; methylation occurs at the 2- and 4-positions in quinoline. 2-Methylquinoline forms inter alia bis(2-quinolyl)methane, tris(2-quinolyl)methane, and 1,2-bis(2-quinolyl)ethane. The results obtained with rhodium-on-carbon are compared with those obtained with degassed Raney nickel.

Illicit heroin manufacturing by-products: capillary gas chromatographic determination and structural elucidation of narcotine- and norlaudanosine-related compounds

1984 ◽  
Vol 56 (14) ◽  
pp. 2940-2947 ◽  
Author(s):  
Andrew C. Allen ◽  
Donald A. Cooper ◽  
James M. Moore ◽  
Manfred. Gloger ◽  
Helmut. Neumann
Keyword(s):  
Chromatographic Determination ◽  
Structural Elucidation ◽  
Related Compounds ◽  
By Products
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