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Reaction of dithio-substituted cinnamyllithium with carbonyl compounds: a test of the HSAB principle

✍ Scribed by Jim-Min Fang; Ming-Yi Chen; Wen-Jin Yang

Book ID
104217673
Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
154 KB
Volume
29
Category
Article
ISSN
0040-4039

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✦ Synopsis

By mediation of BFs.EtsO, dithio-substituted cinnamyllithium 2 reacted predominantly at the o-site with carbonyl compounds. No selectivity was found when the reaction was performed in the absence of BFs.Et20.

We have recently observed the dichotomous regiochemistry of aldehyde and ketone in addition reactions with a lithium anion 1 generated from 2-propenyl-1,3-dithiane.

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Lithium diorganocuprates are now widely used in conjugate additions to a,a-unsaturated car-bony1 compounds' and in coupling reactions with alkyl halides2, allyli~acetates~, and other compounds possessing good leaving groups. Here we report a new reaction of lithium dialkylcuprates which is formally