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For a biography of Adolf Baeyer see: R. Huisgen, Angew. Chem. 1986, 98, 297-311; Angew. Chem. Int. Ed. Engl. 1986, 25, 297-382.
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3
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0344793613
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0344793612
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note
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5" is also one of the best oxygen atom donors with metal catalysts for the generation of high-valent metal-oxo species. For a review see: B. Meunier, New J. Chem. 1992, 16, 203-211.
-
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10
-
-
0345224530
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note
-
A very curious point in the series of the publications of Baeyer and Villiger on peracids and ketone oxidation is that they also discovered the organic peracids and compared them with Caro's acid but they never carried out the reaction that one now has in mind when talking about the Baeyer-Villiger reaction, namely the oxidation of a ketone with an organic peracid.
-
-
-
-
12
-
-
0344793611
-
-
One of these chemical properties was the reaction with benzoyl chloride to form the symmetrical benzoyl peroxide
-
One of these chemical properties was the reaction with benzoyl chloride to form the symmetrical benzoyl peroxide.
-
-
-
-
13
-
-
0345656321
-
-
note
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5, the newly formed sulfate was determined quantitavely by means of the same method. This analysis was optimized by Traube; cf. ref. [22,23]
-
-
-
-
14
-
-
0344793609
-
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The work of Richarz should also be cited here. However, to discuss it in details would be too great a diversion; he reported the electrochemical formation of persulfuric acid and hydrogen peroxide: F. Richarz, Ber. Dtsch. Chem. Ges. 1888, 21, 1669-1674.
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Richarz, F.1
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0345224529
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note
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Berthelot described first the persulfuric acid as being an anhydride. He obtained it by subjecting a well-cooled mixture of sulfurons anhydride and oxygen to the "silent discharge" in an ozone tube. However, the product of this reaction was not stable in solution.
-
-
-
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28
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0345224525
-
-
It is worth mentioning that in spite of the lack of modern spectroscopic methods, product compositions and carbon skeletons were well established
-
It is worth mentioning that in spite of the lack of modern spectroscopic methods, product compositions and carbon skeletons were well established.
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31
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5, but never in an oxidation with peracid.[32] However, Criegee discarded their carbonyl oxide hypothesis from literature by means of chemical transformations as discussed above.[34] So, all three intermediates were only of hypothetical nature without experimental proofs. For recent reviews on the dioxirane chemistry see: [58a] W. Adam, R. Curci, J. O. Edwards, Acc. Chem. Res. 1989, 22, 205-211.
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Additionally, the products are usually acid-sensitive (e.g. transesterifications with TFPAA[72] and acid-catalyzed rearrangements[76]) which restricted the use of strong acids.
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All the runs were made at nearly equivalent ketone concentrations and identical aliquots of the same stock perbenzoic acid solution were employed, in order to keep the catalytic effect of the benzoic acid in the peracid preparation at a constant level to allow reasonable comparisons.
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