Reactions of lignin model beta-aryl ethers with acetyl bromide

被引:11
作者
Lu, FC
Ralph, J
机构
[1] U.S. Dairy Forage Research Center, Agricultural Research Service, University of Wisconsin-Madison, Madison, WI
[2] U.S. Dairy Forage Research Center, USDA Agricultural Research Service, Madison, WI 53706
关键词
acetyl bromide; lignin; lignin model compound; beta-ether; beta-aryl ether; alpha-ether; alpha-aryl ether; benzyl aryl ether; acetylation; bromination;
D O I
10.1515/hfsg.1996.50.4.360
中图分类号
S7 [林业];
学科分类号
0829 ; 0907 ;
摘要
The reactivities of several softwood lignin model compounds with acetyl bromide have been examined in a number of good lignin solvents. Primary (gamma-)alcohols acetylate more rapidly than phenolic hydroxyls, whereas benzylic (alpha-)hydroxyls are converted to bromides via their acetates. Models treated under mild conditions with acetyl bromide cleanly produced acetylated alpha-bromo derivatives. Benzyl aryl ethers are cleaved rapidly and quantitatively to yield aryl acetates and acetylated alpha-bromo products. The rate order for the observed reactions is: primary (gamma-)OH acetylation > benzyl aryl ether cleavage/bromination > benzylic secondary (alpha-)OH acetylation > benzylic acetate to benzylic bromide interconversion much greater than phenolic OH acetylation. These reactions are synthetically useful and have further potential in analytical methodologies.
引用
收藏
页码:360 / 364
页数:5
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