- Highly efficient biphasic ozonolysis of alkenes using a high-throughput film-shear flow reactor
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A new method for ozonolysis of alkenes using a continuous flow film-shear reactor was developed. The reactor uses a shearing microfluidic mixing chamber to provide biphasic mixing of an organic phase and aqueous phase with ozone gas. The H2O acts as an in situ reducing agent for the carbonyl oxide intermediate, providing ketones and aldehydes directly from the reaction mixture. Flow rates of up to 1.0 mmol/min (alkene) with an ozone reaction efficiency of >70% were achieved. Aryl conjugated olefins reacted to form carbonyl species in good yields on a multi-gram scale; however, alkyl olefins reacted with ozone to predominantly form secondary ozonides. The discrepancy in product distributions between alkyl and aryl olefins likely originates from the electronic stability of the carbonyl oxide intermediate, which is longer lived for aryl derivatives due to conjugation.
- Kendall, Alexander J.,Barry, Justin T.,Seidenkranz, Daniel T.,Ryerson, Ajay,Hiatt, Colin,Salazar, Chase A.,Bryant, Dillon J.,Tyler, David R.
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supporting information
p. 1342 - 1345
(2018/03/27)
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- An original on-column oxidative cleavage of vicinal diols using alumina/potassium periodate: Application to sequential oxidation/Horner-Emmons reactions
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An unprecedented simple on-column solvent-free oxidative cleavage of vicinal diols in the solid phase using alumina/potassium metaperiodate is described herein. It permits preparation of the corresponding carbonyl compounds with high purity and good to excellent yields requiring only short reaction times. This methodology is then employed in on-column sequential oxidation/Horner-Emmons reactions for the preparation of selected stilbenes in good yields where both reaction and purification are integrated in a single unit or occur simultaneously permitting the rapid and easy preparation of small samples of pure stilbenes. The on-column oxidative cleavage of vicinal diols using alumina/potassium periodate is investigated. This approach is then applied to sequential oxidation/Horner-Emmons reactions for the simultaneous preparation and purification of stilbenes in good yields and requiring short reaction times.
- Dakdouki, Saada C.,Villemin, Didier,Bar, Nathalie
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experimental part
p. 4448 - 4454
(2011/10/01)
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- Regioselectivity change in the reaction of naphthalene and 2-naphthyl ethers with 1,3,5-triazines depending on reagent quantities
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A new method for the synthesis of 4H-benzo[de]isoquinolin-4-ones has been developed, based on the reaction of 2-naphthyl ethers with an equimolar quantity of 1,3,5-triazines in polyphosphoric acid. With a 2.5 molar excess of 1,3,5-triazines in polyphospho
- Aksenov, Alexander V.,Aksenov, Nicolai A.,Lyakhovnenko, Alexander S.,Aksenova, Inna V.
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experimental part
p. 3439 - 3442
(2010/02/28)
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