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Cubane-forming cyclic dienes that exhibit orthogonal reactivities in the solid state
Journal article   Peer reviewed

Cubane-forming cyclic dienes that exhibit orthogonal reactivities in the solid state

Changan Li, Michael A Sinnwell, Dale C Swenson and Leonard R MacGillivray
Chemical communications (Cambridge, England), Vol.57(55), pp.6725-6727
07/08/2021
DOI: 10.1039/D1CC02725E
PMID: 34126633

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Abstract

Photoirradiation of a binary cocrystal composed of two different cyclic dienes generates a highly-symmetric cubane-like tetraacid cage regioselectively and in quantitative yield. The cage forms by a double [2+2] photodimerization of one of the diene cocrystal components. The second diene while photostable in the cocrystal reacts in a double [2+2] photodimerization as a pure form quantitatively to form a tetramethyl cubane-like cage. The stereochemistry of the cage is structurally authenticated.

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