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The stereochemistry of the cathodic pinacolization of carbonyl compounds: The configuration of benzoin pinacol

✍ Scribed by Richard E. Juday; William L. Waters

Book ID
104224249
Publisher
Elsevier Science
Year
1975
Tongue
French
Weight
124 KB
Volume
16
Category
Article
ISSN
0040-4039

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✦ Synopsis

Previous studies have shown that most aldehydes and unsymmetrical ketones produce mixtures of isomeric glycols when subjected to electropinacolization.' The degree of reduction stereoselectivity has been ascribed to both solution and cathode surface properties. lb, 2 As part of an effort to evaluate the importance of solution vs. electrode effects we studied the electropinacolization of benzoin (,l,). The reduction of Ahas been shown to be highly stereoselective, giving only one of six possible diastereomeric products. 3 Thus, 24 mmol of Lwas reduced in a basic H20/EtOH solution using a mercury-plated copper gauze cathode. The pinacol $, mp 240" dec., was isolated in 50 % yield, the only other product being hydrobenzoin.

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📜 SIMILAR VOLUMES

Electrodimerization IV. Formation of sub
Electrodimerization IV. Formation of substituted pinacols in the reduction of α-substituted carbonyl compounds
✍ C.P. Andrieux; J.M. Savéant 📂 Article 📅 1970 🏛 Elsevier Science ⚖ 288 KB

The electroreduction of a wide variety of aldehydes and ketones substituted on an a aliphatic o r alicyclic carbon has been previously studied. The parent carbonyl compounds were aryl alkyl ketones 1-12 , aliphatic aldehydes and ketones 1!-19 (see also ref. 9 and references therein) and alicyclic ke