55278-23-4

Upstream product

• 136918-14-4 phthalimide 
• 110-83-8 cyclohexene 
• 85-44-9 phthalic anhydride 
• 51971-47-2 1-(1,3-dioxoisoindolin-2-yl)cyclohexane-1-carboxylic acid 
• 107-13-1 acrylonitrile 
• 33081-78-6 sodium phthalimide 

Relevant academic research and scientific papers

[3 + 2] Cycloaddition with photogenerated azomethine ylides in β-cyclodextrin

Stability constants for the inclusion complexes of cyclohexylphthalimide 2 and adamantylphthalimide 3 with β-cyclodextrin (β-CD) were determined by 1H NMR titration, K = 190 ± 50 M?1, and K = 2600 ± 600 M?1, respectively. Photochemical reactivity of the inclusion complexes 2&at;β-CD and 3&at;β-CD was investigated, and we found out that β-CD does not affect the decarboxylation efficiency, while it affects the subsequent photochemical H-abstraction, resulting in different product distribution upon irradiation in the presence of β-CD. The formation of ternary complexes with acrylonitrile (AN) and 2&at;β-CD or 3&at;β-CD was also essayed by 1H NMR. Although the formation of such complexes was suggested, stability constants could not be determined. Irradiation of 2&at;β-CD in the presence of AN in aqueous solution where cycloadduct 7 was formed highly suggests that decarboxylation and [3 + 2] cycloaddition take place in the ternary complex, whereas such a reactivity from bulky adamantane 3 is less likely. This proof of principle that decarboxylation and cycloaddition can be performed in the β-CD cavity has a significant importance for the design of new supramolecular systems for the control of photoreactivity.

Photoinduced SET phthalimidation of unactivated double bonds and its application to the synthesis of protected phenethylamines

Phthalimide, in equilibrium with its conjugate base, adds photochemically to cyclohexene and aryl-substituted alkenes (photophthalimidation). The efficient, predictable regioselective photophthalimidation of styrenes constitutes a synthetically useful process for the preparation of N-phenethyl-phthalimides. A possible mechanism for the photophthalimidation involves the nucleophilic attack of phthalimide anion on the alkene cation-radical generated by single electron transfer to excited phthalimide.

Photocycloaddition of phthalimide anion to alkenes - A highly efficient, convergent method for [2]benzazepine synthesis

The excited state of phthalimide anion adds to cyclic, acyclic and aryl-conjugated alkenes in an efficient and regioselective manner to form [2]benzazepine-1,5-diones, substituted at positions 3 and/or 4. The reaction is independent of the ionization pote

Photophthalimidation of unactivated double bonds. Synthesis of protected phenethylamines

At low hydroxide ion concentrations, the photoaddition of phthalimide to cyclohexene, indene or styrene derivatives takes place. The cation radical obtained in the electron transfer from the alkene to excited phthalimide is trapped by phthalimide anion. At high hydroxide ion concentrations concerted [2+2] cycloaddition occurs that yields benzazepinediones, whatever the ionization potential of the alkene. The most suitable reaction conditions can be inferred from the observed fluorescence of phthalimide anion.

PHOTOCHEMICAL ADDITION OF ALKENES AND ALCOHOLS TO SODIUM PHTHALIMIDE

The results of the photochemical reaction between sodium phthalimide and alkenes (1-hexene and cyclohexene) or alcohols (methanol and tert-butanol) are described.