Diels-Alder Reactions of the [60]Fullerene: From Regularly Functionalized Carbon Spheres to Cyclophanes

Maynollo, Josef; Kräutler, Bernhard

doi:10.1080/10641229608001548

Cited by 13 publications

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“…Following bonding labels in Chart , Scheme depicts the different possibilities for successive formation of multiadducts toward the hexakisadduct species. From this scheme, the multiple additions can proceed through nine unique reaction paths due to symmetry considerations: …”

Section: Resultsmentioning

confidence: 99%

Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C₆₀

1996

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The possibility of successive Diels−Alder cycloadditions of 1,3-butadiene to C60 has been studied theoretically by means of the AM1 semiempirical method. The nine unique possible reaction pathways leading to the experimentally observed T h -symmetric hexakisadduct have been described, and the most thermodynamically favored has been analyzed in more detail. The enthalpy barrier for the cycloaddition changes from 16.2 kcal/mol in the formation of the monoadduct to 17.8 kcal/mol for the hexakisadduct, increasing slightly with successive attacks. However, once the hexakisadduct is reached, addition of a new 1,3-butadiene has an enthalpy barrier as high as 35.5 kcal/mol, in agreement with the fact that experimentally the heptakisadduct has not yet been observed.

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Section: Resultsmentioning

confidence: 99%

Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C₆₀

1996

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Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

2001

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The efficient preparation of monoadducts of [60]fullerene and seven anthracenes (anthracene, 1-methylanthracene, 2-methylanthracene, 9-methylanthracene, 9,10-dimethylanthracene, 2,3,6,7-tetramethylanthracene, and 2,6-di-tert-butylanthracene) by cycloaddition in solution is described. The seven mono-adducts of [60]fullerene and the anthracenes were characterized spectroscopically and were obtained in good yields as crystalline solids. The monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 2-methylanthracene and 9,10-dimethylanthracene crystallized directly from the reaction mixture. The thermolytic decomposition at 180 degrees C of the crystalline monoadducts of [60]fullerene and anthracene, 1-methylanthracene, 9-methylanthracene and 9,10-dimethylanthracene all gave rise to the specific formation of a roughly 1:1 mixture of [60]fullerene and the corresponding antipodal bisadducts ("trans-1"-bisadducts) of [60]fullerene and the anthracenes. In contrast, the crystalline monoadducts of [60]fullerene and the anthracene derivatives 2-methylanthracene, 2,3,6,7-tetramethylanthracene and 2,6-di-tert-butylanthracene all decomposed to [60]fullerene and anthracenes (without detectable formation of bisadducts) upon heating in the solid state to temperatures of 180 to 240 degrees C. The formation of the antipodal bisadducts from thermolytic decomposition of crystalline samples of the monoadducts was rationalized by topochemical control.

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IntermolecularCyclization Reactions to form Carbocycles

Beusker

Scheeren

2009

Patai's Chemistry of Functional Groups

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General Introduction [2 + 2] Cycloaddition Reactions D iels– A lder Reactions [6 + 4] Cycloaddition Reactions [8 + 2] Cycloaddition Reactions [2 + 2 + 2] Cycloaddition Reactions

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Diels-Alder Reactions of the [60]Fullerene: From Regularly Functionalized Carbon Spheres to Cyclophanes

Cited by 13 publications

References 50 publications

Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C₆₀

Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C₆₀

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

IntermolecularCyclization Reactions to form Carbocycles

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Diels-Alder Reactions of the [60]Fullerene: From Regularly Functionalized Carbon Spheres to Cyclophanes

Cited by 13 publications

References 50 publications

Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C60

Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C60

Efficient Preparation of Monoadducts of [60]Fullerene and Anthracenes by Solution Chemistry and Their Thermolytic Decomposition in the Solid State

IntermolecularCyclization Reactions to form Carbocycles

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Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C₆₀

Theoretical Study of the Regioselectivity of Successive 1,3-Butadiene Diels−Alder Cycloadditions to C₆₀