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Substituting Cis-1, 2-dicyano vinyl and synthesis process thereof

A technology for the synthesis of ethylene dicyanide, which is applied to aryl-substituted cis-1, can solve the problems of harm to operators and the environment, low total yield, and difficult separation, and achieve low toxicity of raw materials, high utilization rate, and wide application foreground effect

Inactive Publication Date: 2005-01-05
HEILONGJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The starting materials of this method, sodium cyanide and carbon disulfide, are both highly toxic substances, which are likely to cause harm to operators and the environment. In addition, this method can only synthesize porphyrazine complexes with octaalkylthio groups
The document Zh.Obshch.Khim.1977, 47(9): 2143-2148 once reported that cis-1,2-dibromo-tert-butylethylene was used as raw material to prepare cis-1,2-dicyano-tert The process of butyl ethylene, and document Synthesis.1991,686-688 once reported to take substituted alkyne as raw material, through reactions such as bromination, cyanide and photoisomerization, prepare alkyl or aryl maleonitrile intermediate, this The main disadvantage of the two methods is that pure substances are required for each step of the reaction, especially the substituted trans-1,2-dibromoethylene and the substituted cis-1,2-dibromoethylene have similar properties, and the separation is difficult, and the separated trans-1 , 2-dibromoethylene is not used in the next reaction, so the overall yield of the synthesis is very low and the cost increases

Method used

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  • Substituting Cis-1, 2-dicyano vinyl and synthesis process thereof
  • Substituting Cis-1, 2-dicyano vinyl and synthesis process thereof
  • Substituting Cis-1, 2-dicyano vinyl and synthesis process thereof

Examples

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Embodiment 1

[0029] (1) Synthesis of trans-1,2-dibromo-(4-ethylbenzene)ethylene (1a) and cis-1,2-dibromo-(4-ethylbenzene)ethylene (1a')

[0030] Add 200ml of dry CCl to the reaction flask 4 , 25.0ml of 4-ethylphenylacetylene, 10ml of bromine and 100ml of dry CCl with a dropping funnel 4 The mixed solution of the mixture was slowly dropped into the above-mentioned solution. After the drop was completed, the stirring reaction was continued at room temperature for 4 hours. The reaction solution was washed and the solvent was evaporated to obtain the product trans-1,2-dibromo-(4-ethylbenzene)ethylene ( 1a) and cis-1,2-dibromo-(4-ethylbenzene)ethylene (1a') mixture, the mixture of the two is directly used in the next step reaction, and can also be further purified by column chromatography, weighed, and calculate the yield , Determination of the gas mass spectrometry and infrared spectrum of the product (as in Table 1).

[0031] Table 1 1,2-dibromo-(4-ethylbenzene)ethylene (trans 1a and cis 1a')...

Embodiment 2

[0072] (1) Synthesis of trans-1,2-dibromo-(4-butylbenzene)ethylene (1b) and cis-1,2-dibromo-(4-butylbenzene)ethylene (1b')

[0073] The 4-ethylphenylacetylene in the first step of Example 1 is replaced by equimolar 4-butylphenylacetylene, and the reaction under the same conditions produces trans-1,2-dibromo-(4-butylbenzene) Ethylene (1b) and cis-1,2-dibromo-(4-butylphenyl)ethylene (1b'), the mixture of the two was directly used in the next reaction. Column chromatography can also be used for further purification, weighing, calculating the yield, and measuring the gas-frequency spectrum and infrared spectrum of the product (as shown in Table 1).

[0074] (2) Synthesis of trans-1,2-dicyano-(4-butylbenzene)ethylene (2b) and cis-1,2-dicyano-(4-butylbenzene)ethylene (2b')

[0075] Replace the mixture of trans-1,2-dibromo-(4-ethylbenzene)ethylene and cis-1,2-dibromo-(4-ethylbenzene)ethylene in the second step of Example 1 with trans-1 , 2-dibromo-(4-butylphenyl)ethylene and cis-1,...

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PUM

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Abstract

The invention is a substituted cis-1, 2-ethylene dicyanide and its synthetic method: (1) synthesizing substituted trans-1, 2-ethylene dihalide and substituted cis-1, 2-ethylene dihalide; (2) synthesizing substituted trans-1, 2-ethylene dicyanide and substituted cis-1, 2-ethylene dicyanide; (3) converting substituted trans-1, 2-ethylene dicyanide to the optical isomer of substituted cis-1, 2-ethylene dicyanide; it broadens the modifiability of tetraazaporphyrin complex, and increases the solubility of its metal complex; the synthetic method and conditions are moderate, have no special requirements for the reacting system, the raw materials have low toxicity and the total productivity is high.

Description

technical field [0001] The invention relates to a substituted cis-1,2-dicyanoethylene and a synthesis method thereof, in particular to an alkyl- and aryl-substituted cis-1,2-dicyanide product and a synthesis method thereof. The method of the present invention can be widely used in the synthesis of cis-1,2-dicyanoethylene substituted by alkyl and aryl groups, and its compound and its derivatives are one of the important intermediates for the synthesis of substituted porphyrazine complexes . Background technique [0002] Due to their special macrocyclic structure and excellent physical and chemical properties, porphyrazine and its complexes are widely used in the fields of biology, bionics, materials science, pharmacology, electrochemistry, photophysical chemistry, etc. Cancer photosensitizers, optical storage media, nonlinear optical materials, and humidity-sensitive materials all have very broad application prospects. Due to the poor solubility of unsubstituted porphyrazin...

Claims

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Application Information

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IPC IPC(8): C07C253/00C07C253/30C07C255/09
Inventor 陈志敏吴谊群左霞
Owner HEILONGJIANG UNIV
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