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

Changan Li; Michael A Sinnwell; Dale C Swenson; Leonard R MacGillivray

doi:10.1039/d1cc02725e

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

Chem Commun (Camb). 2021 Jul 8;57(55):6725-6727. doi: 10.1039/d1cc02725e.

Authors

Changan Li¹, Michael A Sinnwell¹, Dale C Swenson¹, Leonard R MacGillivray¹

Affiliation

¹ Department of Chemistry, University of Iowa, Iowa City, IA 52242-1294, USA. len-macgillivray@uiowa.edu.

PMID: 34126633
DOI: 10.1039/d1cc02725e

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.