Oxidative copper trifluoromethanesulfonate

CHROMIUM TRIOXIDE-PYRIDINE COMPLEX, preparation in situ, 55, 84 Chrysene, 58,15, 16 fzans-Cinnamaldehyde, 57, 85 Cinnamaldehyde dimethylacetal, 57, 84 Cinnamyl alcohol, 56,105 58, 9 2-Cinnamylthio-2-thiazoline, 56, 82 Citric acid, 58,43 Citronellal, 58, 107, 112 Cleavage of methyl ethers with iodotri-methylsilane, 59, 35 Cobalt(II) acetylacetonate, 57, 13 Conjugate addition of aryl aldehydes, 59, 53 Copper (I) bromide, 58, 52, 54, 56 59,123 COPPER CATALYZED ARYLATION OF /3-DlCARBONYL COMPOUNDS, 58, 52 Copper (I) chloride, 57, 34 Copper (II) chloride, 56, 10 Copper(I) iodide, 55, 105, 123, 124 Copper(I) oxide, 59, 206 Copper(ll) oxide, 56, 10 Copper salts of carboxylic acids, 59, 127 Copper(l) thiophenoxide, 55, 123 59, 210 Copper(l) trifluoromethanesulfonate, 59, 202... 

Oxidation of a-sulfonyl carbanions with copper(II) trifluoromethanesulfonate gives dimers of the original sulfone, while with copper(II) acetate vinylic sulfones were obtained (Scheme 74). ... 

Copper(I) r-butoxide, 237 Copper(II) chloride, 106 Copper cyanide, 1 Copper(l) iodide, 107 Copper(I) oxide, 107 Copper(II) sulfate, 107 Copperf I) trifluoromethanesulfonate, 108-110... 

The electrophilic substitution is the most characteristic reaction for these classes of compounds. Compound (21) undergoes standard electrophilic aromatic substitution reactions. Thus it forms the 6-bromo compound (58) with A7-bromosuccinimide and 6,7-dibromo compound (72) with the excess of the same reagent. It also forms the 6-nitro compound (67) with copper(II) nitrate trihydrate and 6,7-dinitro compound (68) with excess of nitronium tetrafluoroborate. The bis(trifluoro-acetoxy)thallium derivative (73) was formed from trithiadiazepine (21) and thallium(III) trifluoro-acetate in refluxing acetonitrile. Without isolation, (73) was directly converted into the pale yellow 6-iodo compound (74) with aqueous potassium iodide, into the 6-cyano compound (75) with copper(I) cyanide, and into methyl trithiadiazepine-6-carboxylate (76) with carbon monoxide and methanol in the presence of palladium chloride, lithium chloride, and magnesium oxide. Compound (21) is acetylated in the presence of trifluoromethanesulfonic acid (Scheme 7) <85CC396,87JCS(P1)217, 91JCS(P1)2945>. 

While a-sulfonyl lithiated carbanions are oxidatively coupled with copper(II) trifluoromethanesulfonate (eq 2), Cu(OAc)2 oxidizes them to the corresponding ( )-Q ,/3-unsaturated sulfones (eq 3).13... 

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