Photochemical reduction in the N-acylketimine system

Padwa, Albert; Koehn, William

doi:10.1021/jo00901a005

Cited by 20 publications

(2 citation statements)

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“…113 Padwa and Koehn have also found that the irradiation of a series of /V-(a-alkylbenzylidene)benzamides (60) in hydrogen-donating solvents results in reduction of the carbon-nitrogen double bond. 120 The photoreduction was shown to involve an electronically excited state and did not occur by the chemical Sensitization and emission studies showed that the reaction is derived from an n-rr* triplet state. The failure of the ¡mine nitrogen to initiate Norrish type II reactions in these systems suggests that the intermolecular hydrogen abstraction by the excited /V-acylketimine occurs on the oxygen atom of the carbonyl group rather than on the nitrogen atom of the ¡mine chromophore.…”

Section: Xomentioning

confidence: 99%

Photochemistry of the carbon-nitrogen double bond

Padwa¹

1977

Chem. Rev.

250

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Section: Xomentioning

confidence: 99%

Photochemistry of the carbon-nitrogen double bond

Padwa¹

1977

Chem. Rev.

250

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“…Anal. Caled for NÍC16H35N4O3SF3: Ni,12.24;C,40.08;H,7.36;N,11.69. Found: Ni,12.32;C,40.33; H, 7.35;N,tions similar to those of the methyl complex were generated using diethyl-or diphenylmagnesium in place of the dimethyl compound but products have not been isolated in pure form.…”

mentioning

confidence: 99%

Photochemistry as a probe of the excited state properties of molecules. IV. A determination of the relative triplet reactivities of the carbon-nitrogen and carbon-oxygen chromophores of 4-acylpyrimidines. Photochemical cyclopropanol formation

ALEXANDER¹,

Jackson²

1976

J. Am. Chem. Soc.

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Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

et al. 2023

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The synthesis of four membered heterocycles usually requires multi-step procedures and prefunctionalized reactants. A straightforward alternative is the photochemical [2+2]-heterocycloaddition between an alkene and a carbonyl derivative, conventionally based on the photoexcitation of this latter. However, this approach is limited by the absorption profile of the carbonyl, requiring in most of the cases the use of high-energy UV-light, that often results in undesired side reactions and/or the degradation of the reaction components. The development of new and milder visible light-driven [2+2]-heterocycloadditions is, therefore, highly desirable. In this Review, we highlight the most relevant achievements in the development of [2+2]-heterocycloadditions promoted by visible light, with a particular emphasis on the involved reaction mechanisms. The open challenges will also be discussed, suggesting new possible evolutions, and stimulating new methodological developments in the field. Mechanisms for Visible Light [2+2]-Hetero-CycloadditionsA prerequisite for visible light [2+2]-heterocycloadditions is the presence of a photoactive species able to absorb light

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Photochemical reduction in the N-acylketimine system

Cited by 20 publications

References 12 publications

Photochemistry of the carbon-nitrogen double bond

Photochemistry of the carbon-nitrogen double bond

Photochemistry as a probe of the excited state properties of molecules. IV. A determination of the relative triplet reactivities of the carbon-nitrogen and carbon-oxygen chromophores of 4-acylpyrimidines. Photochemical cyclopropanol formation

Mechanisms and Synthetic Strategies in Visible Light‐Driven [2+2]‐Heterocycloadditions

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