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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 9, 1979 - Issue 4
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Original Articles

Selective Hydrolysis of Thioacetals with Thallium(III) Nitrate

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Pages 301-311 | Received 05 Oct 1978, Published online: 05 Dec 2006
 

Abstract

In connection with research at present being pursued in these laboratories we required quantities of thioacetal (1) for study. Reaction of Wieland-Miescher ketone (2) with one equivalent of 1,2-ethanedithiol gave only (3) resulting from reaction at the α,β-unsaturated carbonyl group. The structure for (3) was deduced primarily from C n. m. r. which showed a saturated carbonyl absorption (δ212.6)1. The preferential reaction of 1,2-ethanedithiol with α,β-unsaturated ketone

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