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Structural re-assignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions

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posted on 2024-11-14, 14:58 authored by Graham E Ball, Glenn Ashley Burley, Leila Chaker, William Hawkins, James Williams, Paul KellerPaul Keller, Stephen PyneStephen Pyne
The addition of N-(diphenylmethylene)glycinate esters (Ph2C=NCH2CO2R) to [60]fullerene under Bingel conditions gives [60]fullerenyldihydropyrroles and not methano[60]fullerenyl iminoesters [C60C(CO2R)(N=CPh2)] as previously reported. Unequivocal evidence for the structure of C60C(CO2Et)(N=CPh2) was provided by INADEQUATE NMR studies on 13C enriched material. New mechanistic details are proposed to account for the formation of [60]fullerenyldihydropyrroles and their reductive ring-opening reactions.

History

Citation

Burley, G., Chaker, L., Hawkins, W., Williams, J., Keller, P. A., Pyne, S. G. & Ball, G. (2005). Structural re-assignment of the mono- and bis-addition products from the addition reactions of N-(diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions. The Journal of Organic Chemistry, 70 8572-8574.

Journal title

Journal of Organic Chemistry

Volume

70

Issue

21

Pagination

8572-8574

Language

English

RIS ID

11970

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