Lignin Chromophores. III. Syntheses of Hydroxy- and Alkoxystilbenes via Aryl Migration
作者:
Josef Gierer,
Nils-Olof Nilvebrant,
期刊:
Journal of Wood Chemistry and Technology
(Taylor Available online 1991)
卷期:
Volume 11,
issue 2
页码: 171-193
ISSN:0277-3813
年代: 1991
DOI:10.1080/02773819108050269
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Stilbenes, representing stilbenoid structures present in residual lignins, have been synthesized by condensation of monochloroacetaldehyde diethylacetal with appropriate phenols and phenol ethers, followed by alkali- or acid-promoted rearrangement of the resulting 1,1-diaryl-2-chloroethanes. It is proposed that the mechanism of these rearrangement steps involves aryl migration with formation of intermediates of the spiro-cyclohexadienone type. The yields of individual stilbenes vary within wide ranges and are in certain cases moderate. However, the method is competitive due to its simplicity and the availability of the starting materials required.
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