THE ACTIVATION OF AMINALS AND AMINOL ETHERS BY SULFUR-DIOXIDE AND THEIR REACTIONS WITH ELECTRON-RICH AROMATIC-COMPOUNDS

Authors
HEANEY H PAPAGEORGIOU G WILKINS RF
Citation
H. Heaney et al., THE ACTIVATION OF AMINALS AND AMINOL ETHERS BY SULFUR-DIOXIDE AND THEIR REACTIONS WITH ELECTRON-RICH AROMATIC-COMPOUNDS, Tetrahedron, 53(39), 1997, pp. 13361-13372
Citations number
35
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
39
Year of publication
1997
Pages
13361 - 13372
Database
ISI
SICI code
0040-4020(1997)53:39<13361:TAOAAA>2.0.ZU;2-6
Abstract
Reactions of bis(dialkylamino)methanes and ethoxydialkylaminomethanes with nucleophilic aromatic heterocycles in the presence of sulfur diox ide result in the formation of the expected Mannich bases in good yiel ds. Reactions of phenols are similarly activated by sulfur dioxide whi ch lead to improved regioselectivity: in particular the reactions of 2 ,5-dimethylphenol result in the formation of 2-dialkylaminomethyl-3,6- dimethylphenol whereas reaction occurs at the 4-position using the cla ssical procedures. (C) 1997 Elsevier Science Ltd.