NBS-promoted oxidation of fullerene monoradicals leading to regioselective 1,4-difunctional fullerenes.
نویسندگان
چکیده
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.
منابع مشابه
Chemistry of fullerene epoxides: synthesis, structure, and nucleophilic substitution-addition reactivity.
Fullerene epoxides, C₆₀O(n), having epoxide groups directly attached to the fullerene cage, constitute an interesting class of fullerene derivatives. In particular, the chemical transformations of fullerene epoxides are expected to play an important role in the development of functionalized fullerenes. This is because such transformations can readily afford a variety of mono- or polyfunctionali...
متن کاملNi-Catalyzed direct 1,4-difunctionalization of [60]fullerene with benzyl bromides.
A new Ni-catalyzed direct 1,4-difunctionalization of [60]fullerene with various benzyl bromides has been developed. The use of a DMSO additive combined with a nickel catalyst is indispensable for the formation of 1,4-dibenzyl fullerenes with a variety of functional groups. The reaction proceeds through the formation of a fullerene monoradical species.
متن کاملREGIOSPECIFIC SYNTHESIS OF 1,6- DIMETHY L-9,lO-ANTHRACENEDIONE
Treatment of acetyl- 1,4-benzoquinone with isoprene gave the corresponding regioselective adduct (I). Rearrangement of the adduct (1) in pyridine and methanol gave 2-acetyl-5, 8-dihydro-6-methyl- 1,4-dihydroxynaphthalene (2). Silver oxide oxidation of the rearranged product (2) gave 2-acetyl-5,8-dihydro- 6-methyl- 1,4naphthalenedione (3). Regioselective addition of trans-piperylene to this...
متن کاملNovel multicomponent reaction of [60]fullerene: the first example of 1,4-dipolar cycloaddition reaction in fullerene chemistry.
The novel multicomponent reaction of [60]fullerene with dimethyl acetylenedicarboxylate and isoquinoline, quinoline or substituted quinolines was investigated. This type of reaction presents the first example of a 1,4-dipolar cycloaddition reaction in fullerene chemistry.
متن کاملA chiral dumbbell shaped bis(fullerene) oligoelectrolyte.
The first icosacationic bis(fullerene) whose water solubility is provided by twenty peripheral ammonium groups has a rigid, almost cylindrical shape and was synthesized by connecting two fullerene cores with a chiral cyclo-bis(malonate), followed by the regioselective addition of ten amino-terminated malonates into the octahedral positions of the fullerene moieties and subsequent cleavage of th...
متن کاملذخیره در منابع من
با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید
برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید
ثبت ناماگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید
ورودعنوان ژورنال:
- Chemical communications
دوره 50 99 شماره
صفحات -
تاریخ انتشار 2014