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

Knichal, Jane V., Shepherd, H.J., Wilson, Chick C., Raithby, Paul R., Gee, William J., Burrows, Andrew D. (2016) An Iodine-Vapor-Induced Cyclization in a Crystalline Molecular Flask. Angewandte Chemie International Edition, 55 (20). pp. 5943-5946. ISSN 1433-7851. (doi:10.1002/anie.201601525) (KAR id:55266)

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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 CHCl3⋅H2O. 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(12H)‐one (hipp).

Item Type: Article
DOI/Identification number: 10.1002/anie.201601525
Subjects: Q Science > QD Chemistry > QD478 Solid State Chemistry
Divisions: Divisions > Division of Natural Sciences > School of Physical Sciences
Depositing User: Helena Shepherd
Date Deposited: 05 May 2016 09:15 UTC
Last Modified: 23 Mar 2021 16:00 UTC
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