Photochemical Reactivity of Keto Imino Ethers. V. (2 + 2) Photocycloaddition to the Carbon-Nitrogen Double Bond of 3-Ethoxyisoindolone
Journal of the American Chemical Society, ISSN: 1520-5126, Vol: 97, Issue: 25, Page: 7288-7298
1975
- 51Citations
- 11Captures
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Article Description
The photochemical reactivity of 3-ethoxyisoindolone (2) with 1,1-dimethoxyethene, cyclohexene, furan, isobutylene, cis-2-butene, trans-2-butene, tetramethylethylene, and fumaronitrile is described. The modes of photochemical reactivity observed include the novel regiospecific (2 + 2) cycloaddition to the carbon-nitrogen double bond of 2 to give products 3, 5, 7, 9, 11, 12, and 18, a photochemical ene type reaction to give products 8,15,16, and 19, and a unique cycloaddition of tetramethylethylene at the 1,2-positions of 2 to give the azepinone 20. The photochemical ene reaction is partially stereospecific but the (2 + 2) cycloaddition reaction is not. The (2 + 2) cycloadducts undergo hydrolytic ring opening to give benzoazepinediones in high yield. The photoreactions of 3-ethoxyisoindolone with olefins occur in high quantum yield from a triplet state, and the singlet state is quenched by the olefins. The mechanism is discussed in terms of a triplet exciplex leading to the ene products and to a long-lived biradical intermediate. © 1975, American Chemical Society. All rights reserved.
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