ChemInform Abstract: Geminal Bond Participation and Reactivities of Z- vs E-1-Substituted Butadienes in the Diels—Alder Reactions.

✍ Scribed by Satoshi Inagaki; Hirotaka Ikeda

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 31 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199912048

✦ Synopsis

Geminal Bond Participation and Reactivities of Z-vs E-1-Substituted Butadienes in the Diels-Alder Reactions. -Analysis of the electronic structures of the transition states in Diels-Alder reactions of butadienes (I)-(VI) with ethylene discloses the significant participation of the geminal σ bonds at the reacting centers in the diene. Electron-donating σ bonds at the Z-positions as in (IVd), (IVe), (Va), (Vb), and (Vc) enhance the reactivity of Z-versus E-butadienes as confirmed by the calculated activation energies of the Diels-Alder reactions. -(INAGAKI, SATOSHI; IKEDA, HIROTAKA;