Journal of Organic Chemistry p. 3614 - 3619 (1987)
Update date:2022-09-26
Topics: Cyclization Photoexcitation Termination Radical Formation Alkene Addition
Somich, Cathleen
Mazzocchi, Paul H.
Ammon, Herman L.
Irradiation of N-methyl-1,8-naphthalimide (NMN) in the presence of α-methylstyrene (α-MS) or 1,1-diphenylethylene in methanol gives novel tetracyclic imides.The mechanism proposed involves photostimulated electron transfer from the alkene to 1,8-NMN and radical coupling addition of methanol to the resultant radical cation-radical anion pair at the 4-position of the aromatic ring to give an unisolable intermediate with an α,β-unsaturated carbonyl moiety.Absorption of a second photon by this chromophore gives rise to the final product.The predicted regiochemistry and stereochemistry of the reaction were established by using pentadeuterio-α-methylstyrene (16), thus providing strong evidence for the mechanism.
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