[2+2] Photocycloaddition of 2‐Morpholinoprop‐2‐enenitrile to Perinaphthenone |
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Authors: | Dietrich Dö pp,Shaaban K. Mohamed,Ahmed El‐Khawaga |
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Abstract: | Perinaphthenone (=1H‐phenalen‐1‐one), known for efficient population of its T1 (π,π*) state and suggested as a standard sensitizer for singlet oxygen (1Δg) formation, forms a single stereoisomer of a head‐to‐tail [2+2] photoadduct across its C(2)=C(3) bond with 2‐morpholinoprop‐2‐enenitrile in benzene by broad band UV excitation (λ≥280 nm). The reaction is advantageously run to low conversion of starting materials only. The structure of the adduct, especially the relative configuration at C(9), has been derived from 1H‐NMR data including NOE signal enhancement studies. |
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