The reaction mechanism of claisen rearrangement obtained by transition state spectroscopy and single direct-dynamics trajectory

Izumi Iwakura*, Yu Kaneko, Shigehiko Hayashi, Atsushi Yabushita, Takayoshi Kobayashi

*Corresponding author for this work

    Research output: Contribution to journalArticlepeer-review

    11 Scopus citations

    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.

    Original languageEnglish
    Pages (from-to)1995-2004
    Number of pages10
    JournalMolecules
    Volume18
    Issue number2
    DOIs
    StatePublished - Feb 2013

    Keywords

    • 5-fs pulse laser
    • Claisen rearrangement
    • Reaction mechanism

    Fingerprint

    Dive into the research topics of 'The reaction mechanism of claisen rearrangement obtained by transition state spectroscopy and single direct-dynamics trajectory'. Together they form a unique fingerprint.

    Cite this