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Synthesis 2012; 44(23): 3693-3698
DOI: 10.1055/s-0032-1317511
DOI: 10.1055/s-0032-1317511
paper
Stereocontrolled Photodimerization of (E)-3-Benzylidene-4-chromanones in the Crystalline State: The Effect of a Halogen Group on the Chromanone Moiety
Weitere Informationen
Publikationsverlauf
Received: 24. August 2012
Accepted after revision: 07. Oktober 2012
Publikationsdatum:
25. Oktober 2012 (online)
Abstract
A series of (E)-3-benzylidene-4-chromanone derivatives are synthesized, which are substituted with a halogen group on the chromanone moiety in order to control the molecular arrangement in the crystalline state. The stereoselective photoreactions of these compounds in the solid state are examined based on the crystal structures of the reactants and products. All the examples tested undergo photodimerization, except for (E)-3-benzylidene-6-fluorochroman-4-one. The reactants with β-structures give syn-head-to-head (syn-HH) products with high selectivity. Only (E)-6-chloro-3-(4-methylbenzylidene)-chroman-4-one adopted the α-form and gives an anti-head-to-tail (anti-HT) product.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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