| Autor: |
Shapiro, E. A., Dolgii, I. E., Nefedov, O. M. |
| Zdroj: |
Russian Chemical Bulletin; September 1980, Vol. 29 Issue: 9 p1493-1499, 7p |
| Abstrakt: |
Conclusions 1.The thermocatalytic reaction of alkyl diazoacetates with gaseous acetylene and methylacetylene proceeds with the formation of the corresponding esters of alkynylacetic acids, the products of the formal insertion of alkoxycarbonylcarbenes at the C-H bond (in up to 50% yields). This process is the main process for acetylene, while for methylacetylene it is accompanied by the formation of the esters of 1-methylcyclopropene-3-carboxylic acids (in up to 16% yields).2.The reaction of ethyl diazoacetate with methylacetylene and dimethylacetylene in the absence of a catalyst leads mainly to the ethyl esters of the corresponding cyclopropene-3-carboxylic acids (in up to 30% yields). At temperatures above 210° the reaction is accompanied by the Wolff rearrangement of ethoxycarbonylcarbene to ethoxyketene, which adds to acetylenes with the formation of 2-ethoxycyclobutenones.3.The ethyl esters of cyclopropene-3-carboxylic acids, which are formed when ethyl diazoacetate is reacted with gaseous methylacetylene and dimethylacetylene, undergo under the reaction conditions, when either CuSO4 or CuO is present, a partial transformation to ethoxyfuran and 2(5H)-furanone derivatives.4.The thermocatalytic reaction of alkyl diazoacetates with steam in a flow reactor leads to the corresponding esters of glycolic acid (in up to 20% yields). |
| Databáze: |
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