Abstract
The reaction rate for the photochemical rearrangement of 1,6-N-(substituted-phenyl)aza-[60]fulleroid 1 to 1,2-N-(substituted-phenyl) aziridino-[60]fullerene 2 differed ca. 3000-fold depending on the position and number of methyl substituents on the N-phenyl group. The required time for the completion of the reaction decreased in the order 2,6-dimethylphenyl (1d) < 2-methylphenyl (1b) < phenyl (1a) < 4-methylphenyl (1c). The difference was mainly due to switching of the excited states between normal (fast reactions) and charge-separated (slow reactions) triplet states, which was induced by steric interactions between the N-phenyl group and the C60 moiety.
Original language | English |
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Pages (from-to) | 6713-6716 |
Number of pages | 4 |
Journal | Tetrahedron Letters |
Volume | 46 |
Issue number | 39 |
DOIs | |
Publication status | Published - 2005 Sep 26 |
Keywords
- Amino compounds
- Fullerenes
- Photochemical reactions
- Reactivity
- Rearrangements
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry