Fa-Bao Li

Synthesis of Fullerooxazoles : Novel Reactions of [60]Fullerene with Nitriles Promoted by Ferric Perchlorate

The ferric perchlorate-mediated reactions of C 60 with various nitriles in o-dichlorobenzene under nitrogen atmosphere afforded the rare fullerooxazoles, which would be difficult to prepare by other methods. A possible reaction mechanism for the formation of the fullerooxazoles was proposed.

Synthesis of Disubstituted [60]Fullerene-Fused Lactones: Ferric Perchlorate-Promoted Reaction of [60]Fullerene with Malonate Esters

The ferric perchlorate-mediated reaction of [60]fullerene with substituted malonate esters in the presence of acetic anhydride afforded the rare disubstituted [60]fullerene-fused lactones. A possible reaction mechanism is proposed.

A facile access to [60]fullerene-fused 1,3-dioxolanes: reaction of [60]fullerene with aldehydes/ketones promoted by ferric perchlorate.

The facile reaction of [60]fullerene (C(60)) with various aldehydes or ketones in the presence of ferric perchlorate successfully afforded the rare C(60)-fused 1,3-dioxolanes. A possible reaction mechanism for the formation of the C(60)-fused 1,3-dioxolanes is proposed.

Synthesis of Fullerene-Fused Lactones and Fullerenyl Esters: Radical Reaction of [60]Fullerene with Carboxylic Acids Promoted by Manganese(III) Acetate and Lead(IV) Acetate

The manganese(III) acetate-mediated radical reaction of [60]fullerene with carboxylic acids in the presence of 4-(dimethylamino)pyridine exclusively afforded the [60]fullerene-fused lactones. Interestingly, the lead(IV) acetate-promoted radical reaction of [60]fullerene with the same carboxylic acids selectively gave another type of fullerene products, i.e., fullerenyl esters. Possible mechanisms for the formation of fullerene products are proposed.

Synthesis of [60]fullerene-fused tetrahydronaphthalene and indane derivatives via a pathway switched by aluminum chloride.

The addition of aluminum chloride to the manganese acetate-mediated radical reaction of [60]fullerene with 2-arylmalonates, 2-benzylmalonates, and 2-arylcyanoacetates can switch the reaction pathway and affords a variety of structurally novel and scarce [60]fullerene-fused tetrahydronaphthalene and indane derivatives. These products are formed probably through radical addition, followed by Friedel-Crafts-type annulation.

Fullerenyl boronic esters: ferric perchlorate-mediated synthesis and functionalization.

Fullerenyl boronic esters have been prepared by a ferric perchlorate-promoted reaction of [60]fullerene with various arylboronic acids. The obtained fullerenyl boronic esters could undergo further functionalization with diols to afford C(60)-fused dioxane/dioxepane derivatives. A possible reaction mechanism for the formation of fullerenyl boronic esters has been proposed.

Ferric Perchlorate-Mediated Synthesis of 1,2-Fullerenols C60(OCOR)(OH)

1,2-Fullerenols C(60)(OCOR)(OH) have been facilely synthesized via the one-step reaction of [60]fullerene with acid chlorides promoted by ferric perchlorate. A possible reaction mechanism for the product formation is proposed.

Synthesis of Ortho Acid Ester-Type 1,3-Dioxolanofullerenes: Radical Reaction of [60]Fullerene with Halocarboxylic Acids Promoted by Lead(IV) Acetate

A lead(IV) acetate-promoted radical reaction of [60]fullerene with halocarboxylic acids has been exploited to synthesize rare ortho acid ester-type 1,3-dioxolanofullerenes, the hydroxyl group of which can be further transformed to an ester or ether group. Intriguingly, an ortho acid ester-type 1,3-dioxolanofullerene can also be converted to a 1,4-dioxanonofullerene in the presence of a base or manipulated to another ortho acid ester-type 1,3-dioxolanofullerene by reaction with a stronger halocarboxylic acid. Moreover, two possible reaction pathways leading to the observed products are also proposed.

Ferric Perchlorate Promoted Reaction of [60]Fullerene with N-Sulfonyl Aldimines: Synthesis and Functionalization of Fulleroxazolidines.

The rare fulleroxazolidines 2 were successfully synthesized by the facile ferric perchlorate promoted reaction of [60]fullerene with various N-sulfonyl aldimines 1. Further functionalization of fulleroxazolidines by arenes in the presence of boron trifluoride afforded 1,4-bisarylation products 4. A possible reaction mechanism for the formation of the fulleroxazolidines is proposed.