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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 31, 2001 - Issue 16
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Original Articles

STEREOSELECTIVE SYNTHESIS OF (Z)-KETENE SELENOTHIOACETALES VIA HYDROZIRCONATION OF LITHIUM ALKYNYLSELENOLATE ANIONS

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Pages 2423-2427 | Received 06 Nov 2000, Published online: 09 Nov 2006
 

Abstract

Lithium alkynylselenolate anions react completely with 1.0 equiv of Cp2Zr(H)Cl in THF at room temperature to give exclusively the α-zirconated vinylselenolate intermediates 3, which by treatment with an alkyl halide afforded the α-zirconated vinyl alkylselenides intermediates 4. Reaction of 4 with alkylsulfenyl chlorides results in the formation of (Z)-ketene selenothioacetals 5 with total control of the regio- and stereochemistry.

Acknowledgments

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