On the π-π interaction in the benzylation of ketones

✍ Scribed by Enrique Díez-Barra; Sonia Merino; Prado Sánchez-Verdú; José Torres

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 466 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00724-2

✦ Synopsis

The benzylation of a set of nine ketones provides enough information to establish how the ketone structure affects the existence of a n-n interaction. The presence of a phenyl moiety starting from the a-carbon atom and flexibility in cyclic ketones are structural features required for effective interactions. The rt-n interaction is controlled by a polar-rt effect. Stronger interaction is achieved when slight electronwithdrawing groups are present in both n-system This results is explained by the predominance of the 6-;t shells attractive interaction in an edge-to-face geometry.