Thermally and photochemically initiated radical chain decomposition of ketone-free methyl(trifluoromethyl)dioxirane

Adam, Waldemar; Curci, Ruggero; González‐Núñez, María Elena; Mello, Rossella

doi:10.1021/ja00020a029

Cited by 91 publications

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“…0.8 M in the parent 1,1,1-trifluoropropanone. Ketone-free solutions of methyl(trifluoromethyl)dioxirane have also been prepared 26,27 by using chlorinated solvents as in the case of dimethyldioxirane. This helped its utilization as an oxidant and made available the study of the thermal and photochemical decomposition of this dioxirane.…”

Section: Methodsmentioning

confidence: 99%

Dioxirane oxidation of sulfur-containing organic compounds

Lévai¹

2003

Arkivoc

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Dedicated to Professor Branko AbstractThis short review describes the utilization of dioxiranes as convenient and extremely efficient electrophilic oxidants for the selective oxidation of sulfur-containing organic compounds. Relevant examples are included to illustrate the chemoselective and stereoselective oxidations of substances with several sites of oxidation. Electrophilic character of the dioxiranes is shown via the oxidation of compounds with two sulfur heteroatoms.

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Section: Methodsmentioning

confidence: 99%

Dioxirane oxidation of sulfur-containing organic compounds

Lévai¹

2003

Arkivoc

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“…The alkyl radical attacks the oxygen atom of another molecule of 2, yielding esters with scrambling of alkyl groups (see Scheme 3, Dioxiranes). 40 The unimolecular rearrangement of dioxiranes to esters may take place only when catalyzed by Lewis acids. 41 These findings shows that the interconvertibility from carbonyl oxides to dioxiranes is not directly related to the formation of rearranged products in solution.…”

Section: Formation Of Esters In Solutionsmentioning

confidence: 99%

Novel aspects of carbonyl oxide chemistry

Ishiguro

Nojima

Sawaki

1997

J. Phys. Org. Chem.

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The structural and chemical properties of 1,3-dipolar peroxidic species (X-O-O) such as ozone (X = O) and carbonyl oxides (X = R 2 C) depend significantly on the nature of X. Although cyclic O 3 is thermodynamically unstable, dioxiranes, cyclic isomers of carbonyl oxides, are isolable and have been fully characterized. In contrast to the well known electrophilic nature of ozone, carbonyl oxides usually act as a nucleophilic oxygen transfer agent, but their reactivity could be altered by substituents. It is expected that the chemistry of R 2 C-O 2 species will provide a good starting point for a better understanding of dioxygen complexes (X-O 2 ) with various Xs. Interesting aspects of carbonyl oxide chemistry are discussed, including methods of generation, cyclization to dioxiranes and the nature of their oxygen transfer activities.

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“…On the other hand, UV light, or traces of certain organic materials or metals, can initiate the fast radical-mediated decomposition of dioxirane 1a in solution. 7 Thus, the purity of solvents and reagents along with the operator's skill are particularly relevant factors in the successful preparation of methyl(trifluoromethyl)dioxirane (1a), and they limit and further discourage the use of this reagent in synthesis.…”

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confidence: 99%

A Simple Protocol for the Generation of Methyl(trifluoromethyl)dioxirane

Mello¹,

González‐Núñez²,

Asensio³

2007

Synlett

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Methyl(trifluoromethyl)dioxirane, generated from an aqueous solution of 1,1,1-trifluoroacetone hydrate, sodium bicarbonate and peroxomonosulfate, is removed from the reaction mixture by the evolved gases and applied to the oxidation of substrates placed in a second reaction zone. The method is simple and robust, and allows for the application of methyl(trifluoromethyl)dioxirane in oxidation reactions on a preparative scale.

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Thermally and photochemically initiated radical chain decomposition of ketone-free methyl(trifluoromethyl)dioxirane

Cited by 91 publications

References 0 publications

Dioxirane oxidation of sulfur-containing organic compounds

Dioxirane oxidation of sulfur-containing organic compounds

Novel aspects of carbonyl oxide chemistry

A Simple Protocol for the Generation of Methyl(trifluoromethyl)dioxirane

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