Stereocontrolled Photodimerization of (E)-3-Benzylidene-4-chromanones in the Crystalline State: The Effect of a Halogen Group on the Chromanone 
Moiety

Xue-Ming Cheng; Min Chen; Zhi-Tang Huang; Qi-Yu Zheng

doi:10.1055/s-0032-1317511

Synthesis, Table of Contents

Synthesis 2012; 44(23): 3693-3698
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

Xue-Ming Cheng

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: zhengqy@iccas.ac.cn

,

Min Chen

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: zhengqy@iccas.ac.cn

,

Zhi-Tang Huang

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: zhengqy@iccas.ac.cn

,

Qi-Yu Zheng*

Beijing National Laboratory for Molecular Sciences, CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. of China Fax: +86(10)62554449 Email: zhengqy@iccas.ac.cn

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Abstract

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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.

Key words

photodimerization - alkenes - photochemistry - chromanones - halogens

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References

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