2,3-Dioxabicyclo[2.2.1]heptane

Porter, Ned A.; Gilmore, Dennis

doi:10.1021/ja00452a053

Cited by 28 publications

(10 citation statements)

References 4 publications

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“…The synthesis of 1,2-dioxanes has been accomplished in various ways. The intramolecular nucleophilic displacement of leaving groups, such as halides8 or mesylates9, has been employed. The use of peroxides as nucleophiles for the intramolecular attack on epoxides is another method for the synthesis of 1,2-dioxanes 10.…”

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confidence: 99%

Palladium(II)-Catalyzed Cyclization of Unsaturated Hydroperoxides for the Synthesis of 1,2-Dioxanes

2009

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confidence: 99%

Palladium(II)-Catalyzed Cyclization of Unsaturated Hydroperoxides for the Synthesis of 1,2-Dioxanes

2009

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“…Mechanistically similar to peroxymercuration, peroxy‐halogenation is more attractive due to a lower toxicity of the reagents and by‐products. [ 13a ] Bloodworth and co‐workers reported the synthesis of bicyclic compounds 9a or 9b by using NBS or NIS, respectively, in deuterated methanol from peroxy‐cyclooctene 8 (Scheme 3). [ 13b ]…”

Section: Nucleophilic Substitution With Hydrogen Peroxide or Hydromentioning

confidence: 99%

“…[ 13a ] Bloodworth and co‐workers reported the synthesis of bicyclic compounds 9a or 9b by using NBS or NIS, respectively, in deuterated methanol from peroxy‐cyclooctene 8 (Scheme 3). [ 13b ]…”

Section: Nucleophilic Substitution With Hydrogen Peroxide or Hydromentioning

confidence: 99%

Synthesis of 3,5‐Disubstituted 1,2‐Dioxolanes

et al. 2020

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Endoperoxides are a source of bioactive compounds which drove to some important anti‐malarial drugs such as artemisinin or arterolane. 1,2‐Dioxolanes drew the attention of many scientists, through the isolation of numerous natural products containing this peroxidized ring structure such as the plakinic acid family or the biosynthetic study of prostaglandins. Thus, a considerable work was reported for the synthesis of such endoperoxides, but mainly applied to the synthesis of 3,3',5,5'‐tetrasubstituted 1,2‐dioxolanes. The recent isolation of new natural products containing a 3,5‐disubstituted dioxolane ring brought our attention on how to specifically prepare such structures. Herein, we tentatively summarize exhaustively all the methods reported for the synthesis of 3,5‐disubstituted 1,2‐dioxolanes. Therefore, nucleophilic substitution with hydrogen peroxide or hydroperoxide, use of electrophilic singlet oxygen, use of triplet oxygen in radical reaction and the chemistry of peroxycarbenium ions will be presented for this purpose.

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“…Silver trifluoroacetate and H 2 O 2 were used also for the synthesis of prostaglandin endoperoxide PGG 2 (2b) 13 236 . While silver acetate promotes a fast and quantitative formation of bicyclic endoperoxide 20 from trans-β-bromohydroperoxide trans-304 (Scheme 74), the parallel reaction with its cis-isomer is sluggish 237 . The structurally more complex bridged bicyclic bromodioxolane 306 was obtained, albeit in very poor yield, by silver(I)-promoted ring closure of 2,3-dibromocyclooctyl hydroperoxide (305) (Scheme 75) 238 .…”

Section: Nucleophilic Substitutionmentioning

confidence: 99%