An Iodine‐Vapor‐Induced Cyclization in a Crystalline Molecular Flask

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  • Jane V. Knichal
    Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UK
  • Helena J. Shepherd
    School of Physical Sciences University of Kent Canterbury Kent CT2 7NH UK
  • Chick C. Wilson
    Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UK
  • Paul R. Raithby
    Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UK
  • William J. Gee
    Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UK
  • Andrew D. Burrows
    Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UK

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<jats:title>Abstract</jats:title><jats:p>A vapor‐induced cyclization has been observed in the host environment of a crystalline molecular flask (CMF), within which 1,8‐bis(2‐phenylethynyl)naphthalene (bpen), a diarenynyl system primed for cyclization, was exposed to iodine vapor to yield the corresponding indeno[2,1‐α]phenalene species. The cyclization process, unique in its vapor‐induced, solvent‐free nature, was followed spectroscopically, and found to occur concurrently with the displacement of lattice solvent for molecular iodine in CMF⋅0.75 bpen⋅2.25 CHCl<jats:sub>3</jats:sub>⋅H<jats:sub>2</jats:sub>O. The cyclization occurred under mild conditions and without the need to suspend the crystals in solvent. The ability of CMFs to host purely gas‐induced reactions is further highlighted by the subsequent sequential oxidation reaction of cyclized 7‐iodo‐12‐phenylindeno[2,1‐α]phenalene (ipp) with molecular oxygen derived from air, yielding 12‐hydroxy‐7‐iodo‐2‐phenylindeno[2,1‐α]phenalen‐1(12<jats:italic>H</jats:italic>)‐one (hipp).</jats:p>

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