Manganese(III) acetate-mediated radical reaction of [60]fullerene with phosphonate esters affording unprecedented separable singly-bonded [60]fullerene dimers.
نویسندگان
چکیده
Radical reaction of [60]fullerene with phosphonate esters mediated by manganese(III) acetate in chlorobenzene afforded singly-bonded fullerene dimers, of which the individual meso and racemic isomers could be unexpectedly separated out for the first time.
منابع مشابه
Reaction of [60]fullerene with free radicals generated from active methylene compounds by manganese(III) acetate dihydrate.
The reaction of [60]fullerene with dimethyl malonate and diethyl malonate in the presence of manganese(III) acetate dihydrate (Mn(OAc)3.2H2O) for 20 min afforded singly bonded [60]fullerene dimers 1a and 1b in a 1,4-addition pattern. When the reaction time was extended to 1 h, 1,4-bisadducts 2a and 2b were obtained. Unsymmetrical 1,4-adduct 5 and C2 symmetrical 1,16-bisadduct 6 were obtained wh...
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[reaction: see text] The reaction of [60]fullerene with 4-substituted phenylhydrazine hydrochlorides in refluxing chlorobenzene under aerobic conditions afforded 1-(4-substituted phenyl)-1,2-dihydro[60]fullerenes, which could be subsequently oxidized to 1-acetoxyl-4-aryl-1,4-dihydro[60]fullerenes by manganese(III) acetate dihydrate in one pot. The transformation of ArC(60)-H to ArC(60)-OAc has ...
متن کاملEvidence for the formation of singly bonded dimers during the reductive electrochemistry of methanofullerenes.
Four methanofullerene derivatives, with phosphonate or sulfone groups attached to a C(60) core through a Bingel procedure, were synthesized to probe their stability upon electrolytic reduction. Derivatives 1 and 2 are the most stable upon electroreduction and do not exhibit retro-cyclopropanation reactions until more than three electrons per C(60) derivative are transferred. The cyclopropane ri...
متن کاملNBS-promoted oxidation of fullerene monoradicals leading to regioselective 1,4-difunctional fullerenes.
We have demonstrated that NBS is able to promote the oxidation of fullerene monoradicals to form 1,4-difunctional fullerenes. The singly bonded fullerene dimers were used as fullerene monoradical precursors, which produced various 1,4-fullerenes with a wide range of functional groups in good to high yields with high regioselectivity in terms of cosolvents and nucleophiles.
متن کاملSilver(I)-mediated three-component annulation reaction of [60]fullerene, sulfonylhydrazones, and nitriles: leading to diverse disubstituted [60]fullerene-fused dihydropyrroles.
A novel Ag(I)-induced three-component annulation reaction of [60]fullerene with sulfonylhydrazones and nitriles has been developed for the efficient synthesis of diverse disubstituted [60]fullerene-fused dihydropyrroles. The reaction exhibits a broad substrate scope and excellent functional-group tolerance, and also allows for the synthesis of fullerene-bound macromolecules.
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ورودعنوان ژورنال:
- Chemical communications
دوره 47 21 شماره
صفحات -
تاریخ انتشار 2011