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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 25, Number 4
BKCSDE 25(4)
April 20, 2004 

 
Title
Lewis Acid-Catalyzed Reactions of Anthrone: Preference for Cycloaddition Reaction over Conjugate Addition Depending on the Functionality of α, β-Unsaturated Carbonyl Compounds
Author
Woonphil Baik*, Cheol Hoon Yoon, Sangho Koo, Hakwon Kim*, Jihan Kim, Jeongryul Kim, Soodong Hong
Keywords
Anthrone, Lewis acid, Cycloaddition, Conjugated addition, Michael reaction
Abstract
The Lewis acid-catalyzed reactions of anthrone with a variety of ethylenic substrates under various conditions have been studied. It has been observed that depending on kinds of ethylenic substrates and catalysts, products were varied. In particular, the ZnCl2-catalyzed reaction of anthrone with α, β-unsaturated ester gave bridged compounds 3 (Diels-Alder adduct type) and mono-Michael adduct 4 exclusively, while the base-catalyzed reaction gave 10,10-bis-Michael adduct as a major product independent of the amount of ethylenic substrate and base. Bridged compounds 3 were easily converted to the corresponding mono-Michael adduct 4 by a catalytic amount of base. Further Michael reaction of mono-Michael adducts with different ethylenic substrates in the presence of a catalytic amount of alkoxide gave unsymmetrical 10,10-bis Michael adducts in good or moderate yields.
Page
491 - 500
Full Text
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