Further Observations on the Reaction of Cyclanones with Perbenzoic Acid

Friess, S.L.; Frankenburg, P. E.

doi:10.1021/ja01130a506

Cited by 27 publications

(10 citation statements)

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“…11 This oxidant has become very inexpensive, 12 and in fact is produced in quantities of ca. 2.4 million metric tons year 21 for use, mainly as a bleach. 13 H 2 O 2 can be a clean oxidant only if it is used in a controlled manner without organic solvents and other toxic compounds.…”

mentioning

confidence: 99%

A green method of adipic acid synthesis: organic solvent- and halide-free oxidation of cycloalkanones with 30% hydrogen peroxide

2003

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Cyclohexanone and cyclohexanol are oxidized to adipic acid in high yield with aqueous 30% H 2 O 2 in the presence of H 2 WO 4 as a catalyst under organic solvent-and halide-free conditions. It is important that no solvent is used in order to achieve high reactivity in this heterogeneous reaction. The use of t-butyl alcohol or dioxane as a solvent (homogeneous conditions) significantly decreases the yield of adipic acid from cyclohexanone. This ketone-to-dicarboxylic acid conversion is applicable to five-to eight-membered cyclic ketones. No operational problems are foreseen for a large-scale version of this green process.

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mentioning

confidence: 99%

A green method of adipic acid synthesis: organic solvent- and halide-free oxidation of cycloalkanones with 30% hydrogen peroxide

2003

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“…T h e fact that v c =~ increases on decreasing the size of a cycloalkanone ring has been known for some time (3). The phenomenon is not restricted t o simple cyclic ketones, for similar compounds with heteroatoms in the ring show the same effect.…”

Section: / Variation Of Vc-0 With Ormentioning

confidence: 60%

The Donor Characteristics of the Carbonyl: Group:ii. The Effect of Angular Variations at the Carbonyl Group

Cook¹

1961

Can. J. Chem.

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The effect of variations in the angle X-C-X' (in a typical carbonyl compound XXIC=O) on the carbonyl stretching frequency (PC-0) is examined in the light of recently published empirical relations between vc ,o and the ionization potential. INTRODUCTIONIn a recent paper dealing with the donor characteristics of the carbonyl group (1) empirical relationships were demonstrated between the carbonyl stretching frequency (vc=,) and the ionization potential (IP). Two classes of compounds were noted: those having no group conjugated with the carbonyl group (A), and those with a group capable of such conjugation (B). The parameters of those molecules were expressed, respectively, by the equations The variation of these parameters within each class was interpreted in terms of inductive and resonance effects due t o the different groups attached t o the carbonyl group.T h e variation of I P with the carbony1 force constant kc=o was considered many years ago by Walsh (2). He pointed out the relationship between IP, kc=o, and C=O bond length and a parameter defining the percentage of polarity of the C=O bond. Since that time Inany more IP's have been accurately measured though the number of determinations of force constants of C=O bonds is still relatively small.Previously (1) no allowance was made for the effect of variations in angle XCX' (a) (in the compound C=O) on v c =~. This will now be considered. x / VARIATION OF vc-0 WITH orT h e fact that v c =~ increases on decreasing the size of a cycloalkanone ring has been known for some time (3). The phenomenon is not restricted t o simple cyclic ketones, for similar compounds with heteroatoms in the ring show the same effect. Figure 1 shows a graph of vc=, and a for a wide variety of cyclic carbonyl compounds, the data and source being listed in Table I. Points lying on the same curve in Fig. 1 are for compounds containing the same functional group, with different ring sizes depending on the number of -CH2-groups contained therein. These lines do not have quite the same slope but get steeper from the bottom line t o the top in a fairly smooth manner.

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“…For example, Furstoss and co-workers relied on enzymes from the fungus E. echinulata to conduct an asymmetric Baeyer-Villiger [20] reaction of cyclobutanone 18 (Scheme 5). [21][22][23][24] The authors then employed the correspond- ing lactone 19 in an enantiodivergent synthesis of (S)-and (R)-proline.…”

Section: Rearrangementmentioning

confidence: 99%

Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity

Sietmann

Wiest

2020

Angew Chem Int Ed

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Cyclobutanones hold a privileged role in enantioselective desymmetrization because their inherent ring strain allows for a variety of unusual reactions to occur. Current strategies include α‐functionalization, rearrangement, and C−C bond activation to directly convert cyclobutanones into a wide range of enantiomerically enriched compounds, including many biologically significant scaffolds. This Minireview provides an overview of state‐of‐the‐art methods that generate complexity from prochiral cyclobutanones in a single operation.

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Further Observations on the Reaction of Cyclanones with Perbenzoic Acid

Cited by 27 publications

References 1 publication

A green method of adipic acid synthesis: organic solvent- and halide-free oxidation of cycloalkanones with 30% hydrogen peroxide

A green method of adipic acid synthesis: organic solvent- and halide-free oxidation of cycloalkanones with 30% hydrogen peroxide

The Donor Characteristics of the Carbonyl: Group:ii. The Effect of Angular Variations at the Carbonyl Group

Enantioselective Desymmetrization of Cyclobutanones: A Speedway to Molecular Complexity

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