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Molecules 2013, 18(2), 1995-2004; doi:10.3390/molecules18021995

The Reaction Mechanism of Claisen Rearrangement Obtained by Transition State Spectroscopy and Single Direct-Dynamics Trajectory

1
Innovative Use of Light and Materials/Life, PREST, JST, 4-1-8 Honcho, Kawaguchi, Saitama 332-0012, Japan
2
University of Electro-Communications, 1-5-1 Chofugaoka, Chofu, Tokyo 182-8585, Japan
3
Department of Chemistry, Graduate School of Science, Kyoto University, Kitashirakawa, Sakyo, Kyoto 606-8502, Japan
4
Department of Electrophysics, National Chiao-Tung University, Hsinchu 300, Taiwan
*
Author to whom correspondence should be addressed.
Received: 9 January 2013 / Revised: 14 January 2013 / Accepted: 28 January 2013 / Published: 4 February 2013
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Abstract

Chemical bond breaking and formation during chemical reactions can be observed using “transition state spectroscopy”. Comparing the measurement result of the transition state spectroscopy with the simulation result of single direct-dynamics trajectory, we have elucidated the reaction dynamics of Claisen rearrangement of allyl vinyl ether. Observed the reaction of the neat sample liquid, we have estimated the time constants of transformation from straight-chain structure to aromatic-like six-membered ring structure forming the C1-C6 bond. The result clarifies that the reaction proceeds via three steps taking longer time than expected from the gas phase calculation. This finding provides new hypothesis and discussions, helping the development of the field of reaction mechanism analysis.
Keywords: Claisen rearrangement; 5-fs pulse laser; reaction mechanism Claisen rearrangement; 5-fs pulse laser; reaction mechanism
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Iwakura, I.; Kaneko, Y.; Hayashi, S.; Yabushita, A.; Kobayashi, T. The Reaction Mechanism of Claisen Rearrangement Obtained by Transition State Spectroscopy and Single Direct-Dynamics Trajectory. Molecules 2013, 18, 1995-2004.

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