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Preparation method for diaryl diazonium methane derivative containing double bonds and application thereof

A technology of diazomethane and derivatives, which is applied in chemical instruments and methods, generation of organic free radicals, production of bulk chemicals, etc., to achieve the effect of low cost and mild reaction conditions

Active Publication Date: 2016-03-23
HARBIN INST OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The present invention aims to solve the problem that the existing method cannot use cheap chemical reagents to prepare a relatively stable carbene active intermediate with functional groups under mild conditions, and provides a double bond-containing bisaryl diazonium Preparation method and application of methane derivative

Method used

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  • Preparation method for diaryl diazonium methane derivative containing double bonds and application thereof
  • Preparation method for diaryl diazonium methane derivative containing double bonds and application thereof

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specific Embodiment approach 1

[0012] Specific embodiment one: the preparation method of a kind of double bond-containing bisaryl diazomethane derivative of this embodiment is specifically carried out according to the following steps:

[0013] 1. First add acetone to 4,4'-dihydroxybenzophenone, then add potassium carbonate, and finally add halogenated olefin, and reflux reaction under stirring conditions for 3h~24h; Distill under reduced pressure to obtain solid I and dry it in vacuum Obtain the benzophenone derivative containing double bond afterwards; The mass of described 4,4'-dihydroxybenzophenone and the volume ratio of acetone are 1g:(1~1000) mL; The 4,4'- The mass ratio of dihydroxybenzophenone and potassium carbonate is 1:(0.02~100); the mass ratio of the 4,4'-dihydroxybenzophenone and halogenated olefin is 1:(0.02~50);

[0014] 2. Add mixed solvent and p-toluenesulfonyl hydrazide to the double bond-containing benzophenone derivative obtained in step 1, reflux for 1d to 5d under stirring conditions,...

specific Embodiment approach 2

[0017] Embodiment 2: This embodiment differs from Embodiment 1 in that the volume ratio of the mass of 4,4'-dihydroxybenzophenone to acetone in step 1 is 1 g:200 mL. Others are the same as in the first embodiment.

specific Embodiment approach 3

[0018] Embodiment 3: The difference between this embodiment and Embodiment 1 or 2 is that the mass ratio of 4,4'-dihydroxybenzophenone to potassium carbonate in Step 1 is 1:10. Others are the same as in the first or second embodiment.

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Abstract

The present invention relates to a preparation method for a diaryl diazonium methane derivative containing double bonds and an application thereof. The present invention aims to solve the problem that a stable carbene reactive intermediate with functional groups cannot be prepared from inexpensive chemistry reagents under mild conditions in the prior art. The method comprises the following steps: taking 4,4'-dihydroxybenzophenone as a raw material, performing substitution reaction on the 4,4'-dihydroxybenzophenone and halogenated olefin, performing hydrazonization reaction on the 4,4'-dihydroxybenzophenone and p-toluenesulfonohydrazide, and removing a p-toluenesulfonyl protecting group under the alkaline condition to obtain the diaryl diazonium methane derivative containing double bonds. According to the preparation method for the diaryl diazonium methane derivative containing double bonds and the application thereof, the diaryl diazonium methane derivative containing double bonds is used as a precursor for preparing the carbene.

Description

technical field [0001] The invention relates to a preparation method and application of a double bond-containing bisaryl diazomethane derivative. Background technique [0002] The chemical grafting method is one of the important methods for surface modification of materials, and has been applied to the regulation of surface properties of various substrates. Carbene is a highly reactive intermediate, which can undergo insertion reaction or addition reaction with the substrate to activate the surface of the material and introduce functional groups. At present, the surface modification of various polymers has been realized by using carbene. It is an ideal precursor for the preparation of carbene from diazomethane derivatives, which can remove diazo groups to generate carbene active centers under heating or light conditions. Due to the delocalization of aryl groups, the chemical properties of bisaryl carbenes are relatively stable, and they are ideal intermediates for surface ...

Claims

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Application Information

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IPC IPC(8): C07C245/16C07B60/00
CPCY02P20/55C07C245/16C07B61/02
Inventor 胡桢宋忱昊黄玉东黎俊
Owner HARBIN INST OF TECH
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