The intramolecular electron transfer reactions of N-Alkylcyclopropyl phthalimides

✍ Scribed by Michele A. Weidner-Wells; Kazuaki Oda; Paul H. Mazzocchi

• Book ID: 104207662
• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 497 KB
• Volume: 53
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(97)00108-7

✦ Synopsis

N-AIkylcyclopropyl phthalimides 5 and 6 were photolyzed to afford spiro tactams 17, 18 and 20-24. These products arise via an intramolecular electron transfer reaction between the phthalimide and the phenylcyclopropane portions of the molecule. The resulting radical anion attacks the phenylcyclopropane radical cation which is followed by radical-radical coupling to afford the observed photoadducts. In addition, the isolation of olefin 19 offers additional proof that the attack of the radical anion onto the radical cation is a stepwise process rather than a concerted one.