EXPERIMENTAL STUDIES OF LEWIS-ACID CATALYZED ADDITIONS OF LONG CHAINED ALCOHOLS TO ACTIVATED 1,4-BENZOQUINONE

Citation
Oeo. Hormi et Am. Moilanen, EXPERIMENTAL STUDIES OF LEWIS-ACID CATALYZED ADDITIONS OF LONG CHAINED ALCOHOLS TO ACTIVATED 1,4-BENZOQUINONE, Tetrahedron, 54(9), 1998, pp. 1943-1952
Citations number
50
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
ISSN journal
00404020
Volume
54
Issue
9
Year of publication
1998
Pages
1943 - 1952
Database
ISI
SICI code
0040-4020(1998)54:9<1943:ESOLCA>2.0.ZU;2-X
Abstract
Lewis acid promoted additions of long chained alcohols to 2-carbometho xy-1,4-benzoquinone (1) have been examined by using various LAs; AlCl3 , TiCl4, MgBr2 and MgCl2. It has been found that the bidentate Lewis a cid MgCl2, having ability to coordinate to both carbonyl oxygens (chel ate control) of 2-carbomethoxy-1,4-benzoquinone (1), produced the addi tion product almost quantitatively at mild conditions. The MgCl2 catal yzed additions of alcohols have been utilized in the synthesis of rare 2-alkoxyhydroquinones (7a-e). The reactions between quinone 1, alcoho l and AlCl3 or TiCl4 have also been investigated by using NMR spectros copy. (C) 1998 Elsevier Science Ltd. All rights reserved.