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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 15
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Original Articles

SYNTHESIS AND HYDROLYTIC STABILITY OF TERT-BUTOXYDIMETHYLSILYL ENOL ETHERS

Zacharia A. Fataftah Department of Chemistry, Yarmouk University, Irbid, Jordan
,
Abdel-Monem M. Rawashdeh Department of Chemistry, University of Missouri-Rolla, Rolla, MO, 65409, U.S.A.
&
Chariklia Sotiriou-Leventis Department of Chemistry, University of Missouri-Rolla, Rolla, MO, 65409, U.S.A.
Pages 2379-2389 | Received 06 Nov 2000, Published online: 09 Nov 2006
 
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Abstract

tert-Butoxydimethylsilyl enol ethers derived from aldehydes and ketones were synthesized in good yields with high regioand stereoselectivities, under thermodynamically and kinetically controlled conditions. The hydrolytic stability of tert-butoxydimethylsilyl enol ether of cyclohexanone was studied under acidic and basic conditions and compared to that of trimethylsilyl, tert-butyldimethylsilyl and (2,4,6-tri-tert-butylphenoxy) dimethylsilyl enol ethers.

ACKNOWLEDGMENT

C. Sotiriou-Leventis thanks the Petroleum Research Fund, administered by the American Chemical Society (Grant No. 35154-AC).

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