Cover Picture: Eur. J. Org. Chem. 21/2002

✍ Scribed by Vilnis Liepins; Jan-E. Bäckvall

• Publisher: John Wiley and Sons
• Year: 2002
• Tongue: English
• Weight: 76 KB
• Volume: 2002
• Category: Article
• ISSN: 1434-193X
• DOI: 10.1002/1099-0690(200211)2002:21<3498::aid-ejoc3498>3.0.co;2-3

✦ Synopsis

COVER PICTURE

The cover picture shows the silylcupration of a 1,3-diene (isoprene) with a silylcopper reagent. The resulting (σ-allyl)copper intermediate has been trapped and characterized by NMR spectroscopy. This intermediate can undergo an electrophilic substitution reaction occurring S E 2 and/or S E 2Ј depending on the electrophile employed. Thus, carbon dioxide gives a selective S E 2Ј reaction, whereas allyl diphenyl phosphate gives a selective S E 2 reaction. Protonolysis of the (σallyl)copper intermediate results in a mixture of both isomers. This method broadens the scope of the silylcupration reaction and provides insight into the mechanism of the reaction. Details are discussed in the article by V.