The relative rates of electron-rich and electron-deficient alkene cycloadditions to benzyne. Enhanced electrophilicity as a consequence of alkyne bending distortions.

✍ Scribed by Nelson G. Rondan; L.N. Domelsmith; K.N. Houk; A.T. Bowne; R.H. Levin

• Publisher: Elsevier Science
• Year: 1979
• Tongue: French
• Weight: 255 KB
• Volume: 20
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)95372-9

✦ Synopsis

Benzyne reacts more rapidly with electron-rich alkenes than electron-deficient alkenes, a result of the abnormally low energy LUMO of benzyne, which results from the acetylene bending enforced by the benzyne geometry.