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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Synthesis and Reactivity of an X-Shaped Molecule: Reversible Formation and Cleavage of a Four-Membered Ring in
Daisuke Asai1, Kazukuni Tahara1
1Department of Applied Chemistry, School of Science and Technology, Meiji University, 1-1-1 Higashimita, Tama-ku, Kawasaki, Kanagawa 214-8571, Japan.
Abstract:
We herein report the synthesis and reactivity of an X-shaped molecule featuring three four-membered rings (4MRs) arranged in a ladder configuration. This molecule exhibits a reversible opening and closure of the central 4MR upon exposure to light irradiation and thermal treatment. The central 4MR of this molecule is also cleaved via electrochemical and chemical reductions. The stimuli-responsiveness of the X-shaped molecule is attributed to the small energy gap difference between its open and closed states, stemming from the antiaromatic character of its precursor.
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