Influence of the Acetylenic Substituent on the Intramolecular Carbolithiation of Alkynes (Eur. J. Org. Chem. 15/2012)

The cover picture shows a crane operating in the harbour of Rouen to unload goods from the ships that sail up the Seine river from the English Channel. In the article by M. Durandetti, J. Maddaluno et al. on p. 2895 ff, the influence of the R terminal substituent of the acetylenic appendage on the c...

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Bibliographic Details
Published in:European journal of organic chemistry 2012-05, Vol.2012 (15), p.n/a
Main Authors: Girard, Anne-Lise, Lhermet, Rudy, Fressigné, Catherine, Durandetti, Muriel, Maddaluno, Jacques
Format: Article
Language:English
Online Access:Get full text
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Summary:The cover picture shows a crane operating in the harbour of Rouen to unload goods from the ships that sail up the Seine river from the English Channel. In the article by M. Durandetti, J. Maddaluno et al. on p. 2895 ff, the influence of the R terminal substituent of the acetylenic appendage on the carbolithiation of the triple bond is described. The results obtained suggest that, in some cases, the interaction between R and the Li cation can explain the surprizing anti selectivity of this reaction. Thus, Li + first acts as a Lewis acid to activate the triple bond and promote the cyclization. It is then “carried” from one side of the newly created exocyclic double bond to the other, as if it were hooked on a crane rotating around its axis. We wish to thank Mr. Jonathan Rangapanaiken for his kind help in preparing the final version of the picture. magnified image
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201290036