Aromatic aldols and 1,5-diketones as optimized fragrance photocages

Griesbeck, Axel G.; Hinze, Olga; Görner, Helmut; Huchel, Ursula; Kropf, Christian; Sundermeier, Uta; Gerke, Thomas

doi:10.1039/c2pp05286e

Cited by 22 publications

(28 citation statements)

References 27 publications

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“…Photochemically triggered hydrolysis of protected volatile aldehydes or ketones has also been demonstrated using 1,5-diketones with abstractable γ-hydrogen 373 or 1-alkoxy-9,10-anthraquinones, e.g., 210 (Scheme 90). 374 The reaction starts with 1,6-hydrogen atom abstraction followed by electron transfer to form the zwitterion 211 , which is trapped by an alcohol.…”

Section: Miscellaneous Groupsmentioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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Section: Miscellaneous Groupsmentioning

confidence: 99%

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

et al. 2012

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“…Contrary to a previous report regarding phthalimide 1, [46] the presence of O 2 quenched the decarboxylation reaction of 4. Assuming that the quenching takes place at a rate of k q = 2 × 10 9 M -1 s -1 , [77] this experiment suggests that the reactive excited triplet state has a lifetime τ ≈ 400 ns. Assuming that the quenching takes place at a rate of k q = 2 × 10 9 M -1 s -1 , [77] this experiment suggests that the reactive excited triplet state has a lifetime τ ≈ 400 ns.…”

Section: Photochemical Reactivitymentioning

confidence: 81%

“…[74,77,82] However, it is unusual that upon excitation to S 2 , the internal conversion into S 1 competes with the ISC. Photochemical reactions of phthalimides from higher excited triplet states have been demonstrated.…”

Section: Photochemical Reactivitymentioning

confidence: 99%

Photodecarboxylation of Adamantane Amino Acids Activated by Phthalimide

et al. 2016

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Adamantane α‐, β‐, and δ‐amino acids activated by phthalimide (i.e., 3–6) were synthesized, and their photochemical reactivities were investigated. Amino acid derivatives 3–6 underwent a photoinduced electron transfer (PET) and decarboxylation reaction sequence, most probably through a triplet excited state. The decarboxylations of the β‐amino acid derivatives were succeeded by cyclization reactions that afforded complex polycyclic molecules with potential biological interest. The adamantyl radical that is produced by the photoinduced decarboxylation could be trapped by alkenes or oxygen to deliver adducts or alcohols, respectively. The photodecarboxylation process was shown to be more efficient under acetone sensitization conditions (with quantum yields, Φ = 0.02–0.5) than upon direct excitation, and the reactivity was dependent on the chain length (intramolecular distance) between the electron donor (carboxylate) and acceptor (phthalimide in the triplet excited state) of the derivative. The formation of different radicals, that is, the 1‐ or 2‐adamantyl intermediate, probably does not affect the overall rate of the decarboxylation This current report provides a better understanding of photodecarboxylation and the rational design of molecular systems to undergo photoinduced decarboxylation and cyclization reactions.

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“…Irradiation of probe 1a in the absence of the singlet oxygen sensitizer Rose Bengal resulted in a very slow buildup of the sulfoxide 1a ox . From comparison of the singlet oxygen quantum yield of Rose Bengal (Φ Δ = 0.75) and the initial 1a ox ‐formation kinetics, Φ Δ for 1a of 0.02 was estimated …”

Section: Resultsmentioning

confidence: 99%

New phthalimide‐methionine dyad‐based fluorescence probes for reactive oxygen species: Singlet oxygen, hydrogen peroxide, and hypochlorite

Griesbeck

Öngel

Atar

2017

J of Physical Organic Chem

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Different reactive oxygen species were detected by the molecular probes 1-3 that were composed of the phthalimide fluorophore as reporter and a methionine-derived thioether side-chain as receptor part. The sulfoxides that were formed as the primary oxidation products show strong fluorescence in the blue-green (430-540 nm) spectral region. Self-sensitized oxidation by singlet oxygen is in general inefficient indicating rapid electron-transfer quenching of the excited probe molecules. With hydrogen peroxide as thermal oxidant conversion to the sulfoxides is slow but can be accelerated by addition of titanium(IV) catalysts, whereas hypochlorite as oxidant behaves much more reactive even under uncatalyzed conditions. Singlet oxygen that is generated by energy transfer from the photosensitizer Rose Bengal was detected by sensor 1a with rate constants of >10 7 M -1 s -1 , a typical rate constant for the oxidation of thioethers to sulfoxides.

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Aromatic aldols and 1,5-diketones as optimized fragrance photocages

Cited by 22 publications

References 27 publications

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Photoremovable Protecting Groups in Chemistry and Biology: Reaction Mechanisms and Efficacy

Photodecarboxylation of Adamantane Amino Acids Activated by Phthalimide

New phthalimide‐methionine dyad‐based fluorescence probes for reactive oxygen species: Singlet oxygen, hydrogen peroxide, and hypochlorite

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