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.

Highlights

  • Taking into consideration that all life on Earth is of organic origin. with carbon as its basic element (20% by weight of every living organism, and the fourth most abundant element in the universe), the discovery in 1985 of its new allotropic modification, fullerene, has resulted in an avalanche-like expansion of studies in this area [1]

  • All of them were synthesized under conditions similar to those indicated in Scheme 24 (Figure 8) [112]

  • Unusual spiromethanofullerenes were presented in reference [157], where the synthesis of N,N-(tetrachlorophthaloyl)dehydroabietylamine derivatives 198–201 from dehydroabietylamine substituted by fullerene in ring B was reported (Scheme 36)

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Summary

Introduction

Taking into consideration that all life on Earth is of organic origin. with carbon as its basic element (20% by weight of every living organism, and the fourth most abundant element in the universe), the discovery in 1985 of its new allotropic modification, fullerene, has resulted in an avalanche-like expansion of studies in this area [1]. C60 adducts were doped with tetrakis(dimethylamino)ethylene (TDAE) and cobaltocene (Cp2Co) in order to create charge-transfer complexes with the purpose of searching for efficient magnetic materials based on fullerenes It can be seen in Scheme 16 that methanofullerene 52 was obtained from the initial, para-substituted, ethyl diazo(4-nitrophenyl)acetate in 32% yield [100]. In the development of new organometallic C60 compounds that can be used as homogeneous catalysts, new blocks 61 and 62, cross-conjugated through cyclopropane, were synthesized (Scheme 19) [104] Attaching such an electron-enriched metal-containing system to C60 can result in push–pull blocks with new electronic and photochemical properties, as demonstrated by complexes 63, [103], and [104] in Scheme 13: Serial synthesis of monophenylmethanofullerenes. All of them were synthesized under conditions similar to those indicated in Scheme 24 (Figure 8) [112]

Synthesis of methanofullerenes with tosylhydrazone
Conclusion
Findings
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