Photochemistry of perester initiators

Thijs, L.; Gupta, Sanjay; Neckers, Douglas C.

doi:10.1021/jo01337a023

Cited by 53 publications

(41 citation statements)

References 1 publication

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“…The efficiency of cleavage results from intramolecular energy transfer from the excited diaryl ketone (triplet energy of ca. 67 kcal/mol). Similar enhancement is seen for peroxyesters tethered to fluorenone .…”

Section: Reactionsmentioning

confidence: 63%

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The Chemistry of Peresters

Locklear

Dussault

2020

Eur J Org Chem

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Section: Reactionsmentioning

confidence: 63%

“…Discussion of intermolecular energy transfer or intramolecular electron transfer can be found in the respective references.…”

Section: Modes Of Reactivitymentioning

confidence: 99%

The Chemistry of Peresters

Locklear

Dussault

2020

Eur J Org Chem

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“…32 Ether cleavage with AlCl 3 in benzene afforded the phenol 1b, which was subjected to alkylation with different alkyl bromides in the presence of a base (NaH or K 2 CO 3 , respectively) to give the esters 1a-3a. Alternatively, following the procedure of Goossen et al, 33 the palladium-catalyzed cross-coupling reaction of 3-methoxybenzeneboronic acid and terephthalic acid monomethyl ester using DSC (di-N-succinimidyl carbonate) as a coupling reagent proceeded smoothly and afforded the ester 4c.…”

Section: Chemistrymentioning

confidence: 99%

Novel 5α-Reductase Inhibitors: Synthesis, Structure−Activity Studies, and Pharmacokinetic Profile of Phenoxybenzoylphenyl Acetic Acids

et al. 2005

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Novel substituted benzoyl benzoic acids and phenylacetic acids 1-14 have been synthesized and evaluated for inhibition of rat and human steroid 5alpha-reductase isozymes 1 and 2. The compounds turned out to be potent and selective human type 2 enzyme inhibitors, exhibiting IC(50) values in the nanomolar range. The phenylacetic acid derivatives were more potent than the analogous benzoic acids. Bromination in the 4-position of the phenoxy moiety led to the strongest inhibitor in this class (12; IC(50) = 5 nM), which was equipotent to finasteride. Since oral absorption is essential for a potential drug, 12 was further examined. In the parallel artificial membrane permeation assay (PAMPA) it turned out to be a good permeator, whereas it was a medium permeator in Caco2 cells. After oral administration (40 mg/kg) to rats a high bioavailability and a biological half-life of 5.5 h were observed, making it a promising candidate for clinical evaluation.

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“…Radicals produced by the cleavage of peresters have been reported as being able to abstract hydrogen atoms from the medium according to ref. 12. Concerning the interaction between BPO and thiopyrylium salt, the photosensitization proceeds mainly through the triplet state of the thiopyrylium.…”

Section: Sensitized Decomposition Of Bttbmentioning

confidence: 99%

Sensitized dissociation of peroxides and peresters in the presence of thiopyrylium salts

Morlet‐Savary¹,

Wieder²,

Fouassier³

1997

Faraday Trans.

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The photosensitized dissociation of peroxides and peresters in the presence of thiopyrylium salts has been studied. The quenching rate constants of the triplet state of the salts under consideration were (3È5) ] 107 l mol~1 s~1 with benzoyl peroxide (BPO) and (3È11) ] 107 l mol~1 s~1 with 3,3@,4,4@-tetra(tert-butylperoxycarbonyl)benzophenone (BTTB) in acetonitrile, the thiopyranyl radical is formed in the presence of BTTB. The mechanism of dissociation photosensitization of these peroxides by pyrylium and thiopyrylium salts is discussed and interpreted in terms of an energy transfer through an electron-exchange mechanism in the case of BTTB and classical energy transfer when BPO is used.

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Photochemistry of perester initiators

Cited by 53 publications

References 1 publication

The Chemistry of Peresters

The Chemistry of Peresters

Novel 5α-Reductase Inhibitors: Synthesis, Structure−Activity Studies, and Pharmacokinetic Profile of Phenoxybenzoylphenyl Acetic Acids

Sensitized dissociation of peroxides and peresters in the presence of thiopyrylium salts

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