[2 + 1] Cycloaddition reactions of fullerene C₆₀ based on diazo compounds

Abstract

The most common variant of fullerene core functionalization is the [2 + 1] cycloaddition process. Of these, reactions leading to methanofullerenes are the most promising. They are synthesized in two main reactions: nucleophilic cyclopropanation according to the Bingel method and thermal addition of diazo compounds. This present review summarizes the material on the synthesis of monofunctionalized methanofullerenes – analogues of [60]PCBM – based on various diazo compounds. The main cyclopropanating agents for the synthesis of monosubstituted methanofullerenes, the optimal conditions and the mechanism of the [2 + 1] cycloaddition, as well as the practical application of the target products are analyzed.

Synthesis and biological application of glyco- and peptide derivatives of fullerene C60

“…For the synthesis of the first fullerene-peptide conjugate [52] in 1993, it was employed a [2+1] cycloaddition reaction [53] by using a diazomethane derivative 1 that once deprotected to a carboxylic acid 3 was coupled to a pentapeptide to form the first fulleryl derivative 6 (Scheme 3).…”

External electric field to control the Diels–Alder reactions of endohedral fullerene

“…4,5 The widespread applicability of fullerene comes from the fact that it can undergo various types of reactions which enables one to modify and change the properties of fullerene for specific purposes. 6,7 In addition, properties of fullerene can also be modified by encapsulating atoms, molecules and metal clusters; known as endohedral fullerenes. [8][9][10][11][12][13] Among the various size of fullerenes, the most representative member is C 60 .…”

“…Similar to benzene, C 60 is also electron-deficient and hence can be easily functionalized through various cycloaddition reactions such as Diels-Alder, Bingel-Hirch, 1-3 dipolar, etc. 6,14,15 Among them, Diels-Alder reaction is considered as one of the most important class of the pericyclic reactions due to its practical and fundamental importance in synthetic organic chemistry.…”

Elucidating the mechanism and reactivity of the reaction between the donor–acceptor–acceptor 1,3-bisdiazo compound and cinnamyl alcohol catalyzed by Rh2(OAc)4: a DFT study

“…The outcomes, i.e. , active carbenoids, can participate in a variety of reactions, for example, cycloaddition, 6,7 ylide formation, 8,9 and X–H functionalization or insertion. 10,11 Among the various cycloadditions, the alkene cyclopropanation reaction is a classical one.…”

“…10,11 Among the various cycloadditions, the alkene cyclopropanation reaction is a classical one. 6,12…”