Synthesis and photosensitized oxygenation of cyclopropylidenecyclobutenes

Sharon, Ofer; Frimer, Aryeh A.

doi:10.1016/j.tet.2003.08.045

Cited by 12 publications

(1 citation statement)

References 55 publications

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“…Recent years have seen a burgeoning in research interest directed toward unraveling the chemistry of singlet oxygen ( 1 O 2 , 1 Δ g ). , This increased attention has been motivated by singlet oxygen’s environmental and biological importance as well as its powerful synthetic potential . Among the reactions of 1 O 2 with unsaturated substrates, the ene or Schenk reaction has received the most extensive experimental and theoretical attention.…”

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confidence: 99%

Stereochemistry of the Singlet Oxygenation of Simple Alkenes: A Stereospecific Transformation

2008

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The stereochemistry of the allylic oxidation (ene reaction) mediated by singlet oxygen ((1)O2), using the optically active alkene (S,S)-cis-1,4-diphenyl-2-butene-1,4-d2 , in MeOH and aprotic solvents was investigated. Our findings indicate that the title reaction is a highly stereospecific suprafacial process, independent of solvent polarity. The observation of an isotope effect, which matches the stereogenic ratio exactly, rules out biradical or open dipolar intermediates.

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confidence: 99%

Stereochemistry of the Singlet Oxygenation of Simple Alkenes: A Stereospecific Transformation

2008

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Hock Rearrangement

2010

Comprehensive Organic Name Reactions and Reagents

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This reaction is protic or Lewis acid–promoted rearrangement of hydroperoxides that have unsaturated unit(s) attached to the carbon bearing the hydroperoxide group to oxycarbonium ion, which undergoes nucleophilic attack by water, leading to the cleavage of C‐C bond and the formation of two carbonyl compounds and is generally referred to as the Hock rearrangement or Hock cleavage. This reaction also occurs in the absence of an added acid and even at temperatures substantially below room temperature. It has been reported that depending on the substrate structure and the choice of Lewis acid, dialkyl peroxide and ozonides might decompose via Hock rearrangement path. This reaction has been applied in the degradation of long hydrocarbon chains with unsaturated unit(s) into carbonyl compounds.

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Spiro[3.3]heptane as a Saturated Benzene Bioisostere**

Prysiazhniuk,

Datsenko,

Polishchuk

et al. 2024

Angewandte Chemie

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The spiro[3.3]heptane core, with the non‐coplanar exit vectors, was shown to be a saturated benzene bioisostere. This scaffold was incorporated into the anticancer drug sonidegib (instead of the meta‐benzene), the anticancer drug vorinostat (instead of the phenyl ring), and the anesthetic drug benzocaine (instead of the para‐benzene). The patent‐free saturated analogs obtained showed a high potency in the corresponding biological assays.

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Synthesis and photosensitized oxygenation of cyclopropylidenecyclobutenes

Cited by 12 publications

References 55 publications

Stereochemistry of the Singlet Oxygenation of Simple Alkenes: A Stereospecific Transformation

Stereochemistry of the Singlet Oxygenation of Simple Alkenes: A Stereospecific Transformation

Hock Rearrangement

Spiro[3.3]heptane as a Saturated Benzene Bioisostere**

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