Synthesis and Properties of Isoxazolo[60]fullerene−Donor Dyads

Abstract

A series of isoxazolo[60]fullerenes has been prepared in one pot from aldoximes under microwave irradiation. Several donors and acceptors were used as substituents. The absorption and emission spectra of these compounds in polar solvents suggest a weak charge-transfer interaction between the oxygen atom of the isoxazoline moiety and the C(60) cage, as well as a stronger interaction between the donor and the fullerene cage when the attached groups are p-N,N-dimethylaniline or ferrocene. The electrochemical properties of the compounds were investigated and they show the same or better acceptor character than C(60) in all cases. Theoretical calculations support the results obtained. Solvent effects in the (1)H NMR spectra have been determined and provide useful information concerning the polarization of dyads.

Microwave assisted synthesis of ferrocene amides

“…b-lactams containing the ferrocene moiety has been synthesized by a one-pot reaction of ferrocenyl acetic acid and achiral or chiral imines with both the conventional thermal methods and the more rapid microwave irradiation technique [12]. Ferrocene containing fulleren derivatives were prepared using microwave heating [13]. According to our knowledge this is the first example of microwave assisted synthesis of the ferrocene amides using N-Ferrocenoyl benzotriazole.…”

Efficient Synthesis of C2v‐Symmetrical Pentakisadducts of C60 as Versatile Building Blocks for Fullerene Architectures that Involve a Mixed Octahedral Addition Pattern

“…[13,14] More recently, it was reported that isoxazolines can also be cleaved under less harsh conditions by heating to reflux in o-dichlorobenzene with an excess amount of a dienophile and Cu II catalysis. [15] We report now a much milder photolytic cleavage of a mixed [5:1]-fullereno isoxazoline adduct 1 prepared from the isoxazolinofullerene 2 [15][16][17] to yield directly C 2v -symmetrical pentakisadducts. The discovery opens now the door to very facile access to complex fullerene-based architectures that involve a mixed octahedral addition pattern.…”

Microwave‐Assisted 1,3‐Dipolar Cycloaddition: an Eco‐Friendly Approach to Five‐Membered Heterocycles

“…The scope of the reaction has been demonstrated by the one-pot preparation of a series of isoxazolino [60]fullerenes 70 in yields ranging from 16 % to 36 %. [61] Scheme 23.…”