Synthesis of epoxyferrocenes by the oxidation of acyl- and allyl-substituted ferrocenes with dimethyldioxirane

Adam, W.; Schuhmann, Rosemarie M.

doi:10.1016/0022-328x(95)05231-d

Cited by 8 publications

(2 citation statements)

References 23 publications

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“…199 The corresponding epoxides are also formed in the oxidation of enol phosphates, 226 g-methylene-g-butyrolactones 227 and acyland allylferrocenes. 228 Epoxidation of primary and secondary alkenylammonium salts by the dioxiranes 1a and 1b gives rise to epoxy derivatives; on treatment with sodium carbonate, they are readily converted into epoxyalkylamines, formed in good yields. 229 The epoxidation rate is lower than that in the case of epoxidation of simple alkenes because the double bonds are deactivated due to the ammonium groups.…”

Section: Oxidation Of Unsaturated Compoundsmentioning

confidence: 99%

Dioxiranes: from oxidative transformations to chemiluminescence

Казаков¹,

Волошин²,

Казаков³

1999

Russ. Chem. Rev.

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Section: Oxidation Of Unsaturated Compoundsmentioning

confidence: 99%

Dioxiranes: from oxidative transformations to chemiluminescence

Казаков¹,

Волошин²,

Казаков³

1999

Russ. Chem. Rev.

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“…In a pioneering work, Wolowiec and Kochi used DMD for the generation of highly unstable oxometal species from Mn(II) and Fe(II) porphyrins and for the oxidative decarbonylation of tricarbonylrhenium and molybdenum complexes . However, is in the release of organic ligands from metal transition complexes and on the selective oxidation of ligands present in these complexes where the reactivity of dioxiranes has been most widely explored. , …”

Section: Introductionmentioning

confidence: 99%

Oxidative Decomplexation of Chromium Fischer Carbene Complexes Induced by Dioxiranes

et al. 1999

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The reaction course of the oxidative decomplexation of Fischer carbene complexes with dioxiranes was examined. The portionwise addition of 2.2 equiv of dimethyldioxirane (DMD) to Fischer carbene complex 1 afforded ethyl phenylpropiolate in 90% yield. When the reaction was carried out using a CO(2)-free DMD solution in a N(2) atmosphere ester 2 was formed in 40% yield, whereas in the presence of an O(2) atmosphere the yield increased to 70%. This same assay performed in the presence of (18)O(2) atmosphere afforded the ester 2 partially labeled at the C=O moiety (approximately 50%, GC-MS) with (18)O. On the other hand, treatment of Fischer carbene complex 1 with a [(18)O(2)]dimesityldioxirane solution led to the formation of (18)O-labeled CO(2) (trapped as BaCO(3) and detected by IRMS). From these results it can be suggested that the oxidative decomplexation of Fischer carbene complexes by dioxiranes involves an initial attack of the dioxirane to the metal coordination sphere. In this step a CO ligand is oxidized to CO(2) thus leaving an unstable chromium tetracarbonyl intermediate which would react with O(2) to give the final ester product and chromium(III) oxide.

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Dioxirane Oxidations of Compounds other than Alkenes

2008

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Epoxidations, heteroatom oxidations, and Y‐H insertions constitute the best investigated oxidations by dioxiranes. This article concerns epoxidation of the double bonds in the cumulenes, such as allenes, acetylenes, and arenes; the oxidation of heteroatom functionalities, mainly lone pairs on sulfur, on nitrogen, and on oxygen as the deoxygenation of N‐ oxides; the oxidation of C = Y functionalities, Y‐H insertions such as in C‐H alkanes, and Si‐H silanes; and the oxidation of organometallic substrates including metal and ligand‐sphere oxidation.

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Synthesis of epoxyferrocenes by the oxidation of acyl- and allyl-substituted ferrocenes with dimethyldioxirane

Cited by 8 publications

References 23 publications

Dioxiranes: from oxidative transformations to chemiluminescence

Dioxiranes: from oxidative transformations to chemiluminescence

Oxidative Decomplexation of Chromium Fischer Carbene Complexes Induced by Dioxiranes

Dioxirane Oxidations of Compounds other than Alkenes

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