Photoinduced hydrogen atom abstraction in N-(adamantyl)phthalimides: structure-reactivity study in the solid state |
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Authors: | Nikola Basari? Margareta Horvat Kata Mlinari?-Majerski Axel G Griesbeck |
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Institution: | a Department of Organic Chemistry and Biochemistry, Ru?er Boškovi? Institute, Bijeni?ka cesta 54, 10000 Zagreb, Croatia b Department of Organic Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany |
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Abstract: | Adamantyl-functionalized phthalimides were synthesized and the probability of intramolecular photochemical hydrogen atom abstraction in the solid state analyzed by X-ray crystallographic analyses. These analyses and solid-state photolyses showed that the parameters determining photochemical reactivity for typical carbonyl compounds in the solid state can also be extended to phthalimides. Only N-(2-adamantyl)phthalimide underwent a solid-state photochemical reaction, which is the first example in the phthalimide series. This reaction is regio- and stereoselective, resulting in an endo-alcohol. On the other hand, the photoreaction of N-(2-adamantyl)phthalimide in solution gives an exo-alcohol as the main product together with an endo-alcohol and a benzazepindione. |
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Keywords: | Adamantane phthalimides Photoinduced H-abstraction Solid-state photochemistry X-ray analysis |
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