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Influence of the Acetylenic Substituent on the Intramolecular Carbolithiation of Alkynes (Eur. J. Org. Chem. 15/2012)
Author(s) -
Girard AnneLise,
Lhermet Rudy,
Fressigné Catherine,
Durandetti Muriel,
Maddaluno Jacques
Publication year - 2012
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201290036
Subject(s) - substituent , chemistry , intramolecular force , triple bond , double bond , stereochemistry , lewis acids and bases , context (archaeology) , medicinal chemistry , catalysis , organic chemistry , paleontology , biology
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.