Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes

Averdung J, Mattay J (1996)
Tetrahedron 52(15): 5407-5420.

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The reaction of C-60 with aryl azides 5 in dichlorobenzene at room temperature leads to isolable triazolinofullerene derivatives 6a and 6b. Photolysis of 6 selectively yields the aziridinofullerenes 7, In contrast to the photolysis the thermolysis affords the azafulleroids 8 as main product next to C-60 In addition the first photochemically induced rearrangement of azafulleroids (1,6-aza-bridged isomers) to aziridinofullerenes (1,2-aza-bridged isomers) is described. Beside aziridines 7 the photochemical reactions of azides 5 with C-60 predominantly yield one novel C-s symmetrical bisadduct, respectively. Furthermore the syntheses of symmetrical 1,2-(3.4-dihydro-2H-pyrrolo)-[60]fullerenes 12a-c by [3+2] cycloaddition of nitrile ylides ii are reported. Copyright (C) 1996 Published by Elsevier Science Ltd
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Averdung J, Mattay J. Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes. Tetrahedron. 1996;52(15):5407-5420.
Averdung, J., & Mattay, J. (1996). Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes. Tetrahedron, 52(15), 5407-5420.
Averdung, J., and Mattay, J. (1996). Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes. Tetrahedron 52, 5407-5420.
Averdung, J., & Mattay, J., 1996. Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes. Tetrahedron, 52(15), p 5407-5420.
J. Averdung and J. Mattay, “Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes”, Tetrahedron, vol. 52, 1996, pp. 5407-5420.
Averdung, J., Mattay, J.: Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes. Tetrahedron. 52, 5407-5420 (1996).
Averdung, J, and Mattay, Jochen. “Exohedral functionalization of [60]fullerene by [3+2] cycloadditions: Syntheses and chemical properties of triazolino-[60]fullerenes and 1,2-(3,4-dihydro-2H-pyrrolo)-[60]fullerenes”. Tetrahedron 52.15 (1996): 5407-5420.
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