Transformations of Peroxide Products of Alkene Ozonolysis

Myasoedova, Yu. V.; Назаров, И. С.; Ishmuratov, G. Yu.

doi:10.1134/s107042801901007x

Cited by 10 publications

(3 citation statements)

References 74 publications

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“…[21][22][23] There are many reagents for the transformation of peroxide products of ozonolysis; both reducing and oxidizing reagents are traditionally used. [24,25] Recently, however, the so-called "nonperoxide" ozonolysis in the presence of peroxide oxygen acceptor compounds (tertiary amines, pyridine), which allows one stage to obtain O-containing compounds without the use of additional reducing agents, [26,27] has attracted interest.…”

Section: Introductionmentioning

confidence: 99%

Ozonolytic transformations of (R)‐(−)‐carvon in the presence of pyridine

Myasoedova

Garifullina

Belyaeva

et al. 2022

J Chinese Chemical Soc

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Ozonolytic transformations of (R)‐(−)‐carvone in aprotic (CH2Cl2) and proton‐donor (MeOH) solvents in the presence of pyridine were carried out. A low conversion of the starting diene was noted when carrying out controlled ozonolysis by treatment with equivalent of О3. A mixture of 3‐acetyl‐5‐methoxy‐5‐oxopentanoic acid and methyl 4‐oxo‐3‐(2‐oxoethyl)pentanoate in MeOH and 5‐acetyl‐2‐methylcyclohex‐2‐en‐1‐one in CH2Cl2 were formed. Exhaustive ozonolysis of (R)‐(−)‐carvone in CH2Cl2 in the presence of pyridine leads to 3‐acetylpentadioic acid. The monomethyl ether of 3‐acetylpentadioic acid and the product of its cyclization—2,8‐dioxo‐1‐methylbicyclo[3.3.0]octane‐3,7‐dione were formed in MeOH/Py by the treatment of ozone excess.

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Section: Introductionmentioning

confidence: 99%

Ozonolytic transformations of (R)‐(−)‐carvon in the presence of pyridine

Myasoedova

Garifullina

Belyaeva

et al. 2022

J Chinese Chemical Soc

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“…Flow chemistry appears as a viable alternative approach, both in terms of risk management ,− and environment control as it involves a low reactive inventory. There has been significant interest in developing ozonolysis reactions in flow − including scale-up aspects, as well as pharmaceutically relevant targets. − …”

Section: Introductionmentioning

confidence: 99%

Scale-Up of Ozonolysis using Inherently Safer Technology in Continuous Flow under Pressure: Case Study on β-Pinene

Vaz

Courboin

Winter

et al. 2021

Org. Process Res. Dev.

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Despite its synthetic relevance, ozonolysis is still an underused reaction in the synthetic chemistry industries. This can be attributed to safety issues while handling the ozone itself, alongside extra hazard related to unstable reaction intermediates. Flow chemistry is inherently safer as it involves a small volume of reagent at any given time. Here, to address safety and technical issues, we describe the design and testing of an ozone dosing line. A global risk assessment and the description of the setup, the analytics, are presented in detail. This new dosing line enabled the successful scale-up of β-pinene ozonolysis in flow, with a productivity of over 16 g/h.

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“…Selective cleavage and reassembly of CC double bonds provide powerful strategies to construct high-valued chemicals . In this regard, many methods such as olefin metathesis, ozonolysis, transition-metal catalysis, and photocatalysis have been developed to cleave the CC double bonds (Scheme a). Although significant progress has been achieved, the cleavage and reassembly of the CC double bonds located in one product molecule are rarely achieved for the relevant synthesis of complex heterocyclic compounds (especially pharmaceuticals) without transition metals .…”

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confidence: 99%

PhIO-Mediated Oxidative C═C Bond Cleavage and Reassembly toward Highly Functionalized Oxazolones

2022

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An efficient PhIO-mediated oxidative CC bond cleavage and reassembly of enaminone toward oxazolone with high regioselectivity has been reported. DFT calculations revealed that the reaction proceeded through an oxygen atom transfer, CC bond cleavage, alkylthio migration, and reassembly cascade. This strategy is highlighted by high atom and step economy with formation of five bonds in one pot and generation of a high-valued oxazolone skeleton under mild conditions.

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Transformations of Peroxide Products of Alkene Ozonolysis

Cited by 10 publications

References 74 publications

Ozonolytic transformations of (R)‐(−)‐carvon in the presence of pyridine

Ozonolytic transformations of (R)‐(−)‐carvon in the presence of pyridine

Scale-Up of Ozonolysis using Inherently Safer Technology in Continuous Flow under Pressure: Case Study on β-Pinene

PhIO-Mediated Oxidative C═C Bond Cleavage and Reassembly toward Highly Functionalized Oxazolones

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