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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 1
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Original Articles

The Hydroxide-Initiated Cleavage of α-Diketone Monothioketals

James A. Marshall Department of Chemistry, Northwestern University, Evanston, Illinois, 60201
,
Charles T. Buse Department of Chemistry, Northwestern University, Evanston, Illinois, 60201
&
David E. Seitz Department of Chemistry, Northwestern University, Evanston, Illinois, 60201
Pages 85-88 | Received 12 Dec 1972, Published online: 06 Dec 2006
 
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Abstract

Recently we reported a presumed nucleophile induced carbon-carbon bond cleavage of α-diketone monothioketals to give thioketal-carboxylates.1 At the time we envisioned this cleavage reaction as proceeding along the following lines (Scheme I).

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