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Reactions of acyl anions generated from acid chlorides and diiodosamarium

✍ Scribed by J. Souppe; J-L. Namy; H.B. Kagan

Publisher
Elsevier Science
Year
1984
Tongue
French
Weight
224 KB
Volume
25
Category
Article
ISSN
0040-4039

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✦ Synopsis

Acid chlorides react with Sm12 to give a-diketones.Various experiments show that theinitially formed acyl radical is rapidly transformed into an acyl anion which is thus generated byquite an unusual route. This species acylates acid chlorides, aldehydes and ketones in situ to give a-diketones and a-ketols. There are some limitations to this acyl anion chemistry but the reactions arerealized with a good efficiency at room temperature in THF solution.

We recently described' a new method for the formation of symmetrical a-diketones, using Sm12' as the coupling agent :

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## Abstract Reactions of aminonitriles 1a–e with disubstituted acetylenes 2, 3, carried out in DMSO in the presence of powdered sodium hydroxide and benzyltriethylammonium chloride (TEBAC) as a catalyst, afford either 4 and 5 or a mixture of 4 and 6; unmasking of the carbonyl group in 5a and 6a giv