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Unexpected reactivity of oxygenated 2-acyl-1,3-dithianes with electrophiles

✍ Scribed by Michael Smietana; Alain Valleix; Charles Mioskowski


Publisher
Elsevier Science
Year
2003
Tongue
French
Weight
208 KB
Volume
44
Category
Article
ISSN
0040-4039

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✦ Synopsis


Lithium enolates of oxygenated acyl-dithiane undergo unexpected regiospecific reactions with electrophiles. Reaction of aldehydes with oxygenated acyl-dithiane leads to the formation of the corresponding monosubstituted b-hydroxy-acyl-dithiane.


πŸ“œ SIMILAR VOLUMES


A mild cleavage of 1,3-diketones: Prepar
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A mild method for cleaving 1,3-diketones is described. The products are 2-acyldithianes and these R-Csynthons can be alkylated under mildly basic conditions. Acetylacetone (1) reacted with propane-1,3-dithio tosylate (2) in methanol to give 2-acetyl-1,3-dithiane + (3) (82%), whose 'H-n.m.r. spectrum

Electrophilic Reactivities of 1,2-Diaza-
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## Abstract The kinetics of the reactions of 1,2‐diaza‐1,3‐dienes **1** with acceptor‐substituted carbanions **2** have been studied at 20 °C. The reactions follow a second‐order rate law, and can be described by the linear free energy relationship log __k__(20 °C)=__s__(__N__+__E__) [Eq.β€…(1)]. Wit