Fe(II)-mediated fragmentation of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes through competitive single electron transfer pathway and Lewis acid pathway

Kamata, Masaki; Kudoh, Takashi; Kaneko, Jun-ichi; Kim, Hye‐Sook; Wataya, Yusuke

doi:10.1016/s0040-4039(01)02201-8

Cited by 9 publications

(2 citation statements)

References 24 publications

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“…The formation of ketone 26 may have been initiated by trace metal catalysis. Numerous metals are known to induce the peroxide bond cleavage of cyclic endoperoxides, followed by a 1,5-hydrogen atom abstraction to yield 4-hydroxy ketones of type 26 . , It is also possible that ketone byproduct, although not isolated, may be responsible for the relatively low yields of dihydroxylated compounds 23 and 24 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols

et al. 2008

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Section: Resultsmentioning

confidence: 99%

Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols

et al. 2008

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“…21 Compound 2 is the first p-terphenyl possessing such a moiety. Compound 3 is structurally related to the synthetic compound 1,4-bis(4-methoxyphenyl)-7-oxabicyclo[2.2.1]heptane, 22 but differs by having different substituents on the central moiety, representing the first naturally occurring p-terphenyl with such a substructure. Compound 4 is closely related to the fungal metabolite gliocladinin A, 23 but differs in the substituents, substitution pattern, and the identity of the central ring.…”

Section: Journal Of Natural Productsmentioning

confidence: 99%

Hawaiienols A–D, Highly Oxygenated p-Terphenyls from an Insect-Associated Fungus, Paraconiothyrium hawaiiense

Ren¹,

Chen

Zhang³

et al. 2018

J. Nat. Prod.

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Four new highly oxygenated p-terphenyls, hawaiienols A-D (1-4), have been isolated from cultures of Paraconiothyrium hawaiiense, a fungus associated with the Septobasidium-infected insect Diaspidiotus sp.; their structures were elucidated primarily by NMR experiments. The absolute configurations of 1 and 2-4 were assigned by single-crystal X-ray diffraction analysis using Cu Kα radiation and via electronic circular dichroism calculations, respectively. Compound 1 incorporated the first naturally occurring 4,7-dioxatricyclo[3.2.1.0]octane unit in its p-terphenyl skeleton and showed cytotoxicity toward six human tumor cell lines.

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BIAN‐Fe(η⁶‐C₆H₆): Synthesis, characterization, and l‐lactide polymerization

Brown

Wekesa

Unruh

et al. 2017

J. Polym. Sci. Part A: Polym. Chem.

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The a-diimine-ligated Fe-complex, BIAN-Fe(C 6 H 6 ), was synthesized and evaluated for the polymerization of L-lactide. Characterization of BIAN-Fe(C 6 H 6 ) reveals that it is redox non-innocent and suggests that it is an Fe(I) species bearing a radical-anionic ligand. We will demonstrate that BIAN-Fe(C 6 H 6 ) is active for the ring-opening polymerization of L-lactide, and that polymer is produced with, or without, the use of an added external initiator. Interestingly, very high molecular weight polymers are produced in the absence of external initiator whereas polymer molecular weights that agree with theoretical calculations are produced in the presence of external initiator. To the best of our knowledge, BIAN-Fe(C 6 H 6 ) is the first Febased a-diimine catalyst reported to be active for the polymerization of L-lactide.

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Fe(II)-mediated fragmentation of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes through competitive single electron transfer pathway and Lewis acid pathway

Cited by 9 publications

References 24 publications

Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols

Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols

Hawaiienols A–D, Highly Oxygenated p-Terphenyls from an Insect-Associated Fungus, Paraconiothyrium hawaiiense

BIAN‐Fe(η⁶‐C₆H₆): Synthesis, characterization, and l‐lactide polymerization

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Fe(II)-mediated fragmentation of 1,4-diaryl-2,3-dioxabicyclo[2.2.2]octanes through competitive single electron transfer pathway and Lewis acid pathway

Cited by 9 publications

References 24 publications

Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols

Synthesis and Chemistry of 2,3-Dioxabicyclo[2.2.2]octane-5,6-diols

Hawaiienols A–D, Highly Oxygenated p-Terphenyls from an Insect-Associated Fungus, Paraconiothyrium hawaiiense

BIAN‐Fe(η6‐C6H6): Synthesis, characterization, and l‐lactide polymerization

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BIAN‐Fe(η⁶‐C₆H₆): Synthesis, characterization, and l‐lactide polymerization