Convenient synthesis of hexasubstituted benzene derivatives via DABCO promoted domino reaction of arylidene malononitrile and dialkyl but-2-ynedioate

A DABCO catalyzed domino reaction between 3-oxo-4-(2-oxoindolin-3-ylidene) butanoates and allenoates furnished 2,3,5-substituted tetrahydrofuran furan derivatives bearing oxindole moiety and two exocyclic double bonds in high yield.

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Copper(II)‐catalyzed Domino Reaction of the Acyclic Ketene‐( S , S )‐Acetals with Diazo Compounds: Convenient Synthesis of Poly‐substituted Thiophenes

Advanced Synthesis & Catalysis ◽

10.1002/adsc.201901089 ◽

2019 ◽

Vol 361 (24) ◽

pp. 5684-5689 ◽

Cited By ~ 4

Author(s):

Ran Sun ◽

Yang Du ◽

Cui Tian ◽

Lei Li ◽

He Wang ◽

...

Keyword(s):

Diazo Compounds ◽

Domino Reaction ◽

Convenient Synthesis

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Coefficients of molecular homeomorphism and crystalline isomorphism in the series of para-disubstituted benzene derivatives

Journal de Chimie Physique ◽

10.1051/jcp/1991880509 ◽

1991 ◽

Vol 88 ◽

pp. 509-514 ◽

Cited By ~ 4

Author(s):

MA Cuevas Diarte ◽

T Calvet ◽

M Labrador ◽

E Estop ◽

HAJ Oonk ◽

...

Keyword(s):

Benzene Derivatives ◽

Disubstituted Benzene

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Silicon Assisted Halogenation I: A Convenient Synthesis of β-chloroketones via Reaction of α,β-unsaturated ketones with Tetrachlorosilane-Phenol

10.3390/ecsoc-13-00181 ◽

2009 ◽

Author(s):

Tarek Salama ◽

Saad Elmorsy

Keyword(s):

Unsaturated Ketones ◽

Convenient Synthesis

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Arene Dearomatization via Radical Hydroarylation

10.26434/chemrxiv.9874454 ◽

2019 ◽

Cited By ~ 1

Author(s):

Autumn Flynn ◽

Kelly McDaniel ◽

Meredith Hughes ◽

David Vogt ◽

Nathan Jui

Keyword(s):

Precious Metal ◽

Room Temperature ◽

Aryl Halide ◽

Solvent System ◽

Benzene Derivatives ◽

Green Solvent ◽

Photocatalytic System

A photocatalytic system for the dearomative hydroarylation of benzene derivatives has been developed. Using a combination of an organic photoredox catalyst and an amine reductant, this process operates through a reductive radical-polar crossover mechanism where aryl halide reduction triggers a regioselective cyclization event, giving rise to a range of complex spirocyclic cyclohexadienes. This light-driven protocol functions at room temperature in a green solvent system (aq. MeCN), without the need for precious metal-based catalysts or reagents, or the generation of stoichiometric metal byproducts.

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Convenient Synthesis of (Z)-7- and (E)-9-dodecene-1-yl Acetate, Components of Some Lepidoptera Insect Sex Pheromone

Revista de Chimie ◽

10.37358/rc.17.1.5415 ◽

2017 ◽

Vol 68 (1) ◽

pp. 180-185

Author(s):

Adriana Maria Andreica ◽

Lucia Gansca ◽

Irina Ciotlaus ◽

Ioan Oprean

Keyword(s):

Sex Pheromone ◽

Coupling Reaction ◽

Coupling Scheme ◽

Lithium Aluminium Hydride ◽

Terminal Alkyne ◽

Mercury Derivative ◽

Lithium Aluminium ◽

Convenient Synthesis ◽

Practical Synthesis ◽

Insect Sex

Were developed new and practical synthesis of (Z)-7-dodecene-1-yl acetate and (E)-9-dodecene-1-yl acetate. The routes involve, as the key step, the use of the mercury derivative of the terminal-alkyne w-functionalised as intermediate. The synthesis of (Z)-7-dodecene-1-yl acetate was based on a C6+C2=C8 and C8+C4=C12 coupling scheme, starting from 1,6-hexane-diol. The first coupling reaction took place between 1-tert-butoxy-6-bromo-hexane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-oct-7-yne, which is transformed in di[tert-butoxy-oct-7-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromobutane obtaining 1-tert-butoxy-dodec-7-yne. After acetylation and reduction with lithium aluminium hydride of 7-dodecyne-1-yl acetate gave (Z)-7-dodecene-1-yl acetate with 96 % purity. The synthesis of (E)-9-dodecene-1-yl acetate was based on a C8+C2=C10 and C10+C2=C12 coupling scheme, starting from 1,8-octane-diol. The first coupling reaction took place between 1-tert-butoxy-8-bromo-octane and lithium acetylide-ethylendiamine complex obtaining 1-tert-butoxy-dec-9-yne, which is transformed in di[tert-butoxy-dec-9-yne]mercury. The mercury derivative was directly lithiated and then alkylated with 1-bromoethane obtaining 1-tert-butoxy-dodec-9-yne. After reduction with lithium aluminium hydride of 1-tert-butoxy-(E)-9-dodecene and acetylation was obtained (E)-9-dodecene-1-yl acetate with 97 % purity.

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Toxicity of Para-Chloro Substituted Benzene Derivatives in the Microtox™ Test

Water Quality Research Journal ◽

10.2166/wqrj.1985.016 ◽

1985 ◽

Vol 20 (2) ◽

pp. 36-43 ◽

Cited By ~ 9

Author(s):

Klaus L.E. Kaiser ◽

Juan M. Ribo ◽

Brian M. Zaruk

Keyword(s):

General Formula ◽

Functional Group ◽

Structural Parameters ◽

Systematic Investigation ◽

Photobacterium Phosphoreum ◽

Benzene Derivatives ◽

Quantitative Structure ◽

Chlorinated Benzenes ◽

Chloro Derivatives ◽

Derivatives Of

Abstract This paper gives the results of part of a systematic investigation into contaminant toxicity to Photobacterium phosphoreum in the Microtox™ test. Reported are the toxicity values for 39 para-chloro substituted benzene derivatives of the general formula l-Cl-C6h4-4-X=CH2CH(NH2)COOH, F, SO2NH2, OCH2COOH, CH2COOH, CONHNH2, NHCOCH3, CONH2, CH=CHCOOH, SeOOH, CH2NH2, CH2CH2NH2, NO2, H, CF3, CHO, CH2OH, OH, CH3, CCl3, COCH3, COOH, NH2, SO2C6H5, Cl, CH2COCH3, COCl, CN, OCH3, NCO, NHCH3, I, COC6H5, CH2Cl, SH, CH2SH, NCS, CH2CN and SO2C6H4Cl. Except for the last compound, whose solubility is below the required concentration, the toxicities increase in the presented order with a total range of more than three orders of magnitude. The data are discussed in terms of quantitative structure-toxicity correlations with compound-specific structural parameters. In combination with a previously developed submodel on chlorinated benzenes, phenols, nitrobenzenes and anilines, the observed relationships allow the prediction of the toxicity of some 780 possible chloro derivatives of the general formula C6H5-nClnX, where n=<5 and X is a functional group as listed above.

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