Reaction of [60]fullerene with trans-epoxides: a theoretical study
- 16 March 2009
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Organic & Biomolecular Chemistry
- Vol. 7 (9), 1851-1857
- https://doi.org/10.1039/b818965j
Abstract
The experimental results of the reaction of C60 with carbonyl ylides generated from trans-epoxides, which afforded cis-products exclusively or predominantly, can be explained well by computational investigation of the proposed reaction mechanism. Our theoretical calculations demonstrate that only cis-carbonyl ylides can be formed directly from trans-epoxides, in compliance with the Woodward–Hoffmann rule. Importantly, the ring opening of trans-epoxides, which is the rate-determining step, should be included in the whole reaction profiles to explain all experimental phenomena.Keywords
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