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Issue 43, 2019

Regioselective [2 + 2] cycloaddition reaction within a pair of polymorphic co-crystals based upon halogen bonding interactions

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Abstract

The realization of a pair of photoreactive polymorphic co-crystals that are held together by the combination of I⋯N halogen bonding interactions and C–H⋯Cl contacts is reported. The reactant molecule within these co-crystals is based upon an unsymmetrical olefin, namely 4-stilbazole, that results in a regioselective solid-state [2 + 2] cycloaddition reaction in both polymorphic forms. Each solid undergoes a quantitative photoreaction which yields exclusively the head-to-tail photoproduct.

Graphical abstract: Regioselective [2 + 2] cycloaddition reaction within a pair of polymorphic co-crystals based upon halogen bonding interactions

Supplementary files

Article information


Submitted
01 Sep 2019
Accepted
12 Oct 2019
First published
14 Oct 2019

CrystEngComm, 2019,21, 6671-6675
Article type
Paper
Author version available

Regioselective [2 + 2] cycloaddition reaction within a pair of polymorphic co-crystals based upon halogen bonding interactions

E. Bosch, S. J. Kruse, E. W. Reinheimer, N. P. Rath and R. H. Groeneman, CrystEngComm, 2019, 21, 6671 DOI: 10.1039/C9CE01379B

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