Journal
TETRAHEDRON LETTERS
Volume 54, Issue 30, Pages 3997-4000Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2013.05.075
Keywords
Cation-pi interaction; Bispyridylethylene; [2+2] Photodimerization; Catalysis; Stereoselective reaction
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Funding
- MEXT
- Grants-in-Aid for Scientific Research [24105508] Funding Source: KAKEN
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Irradiation of trans-4,4'-bispyridylethylene in the presence of I equiv of concd HCl produced a syn dimer with high selectivity, whereas irradiation in the presence of more than 2 equiv of concd HCl or in the absence of HCl gave a mixture of dimers and by-products with much lower selectivity. This indicated that a suitable amount of acid served as a catalyst for the [2+2] photodimerization of BPEs through cation-pi interactions between the pyridinium and pyridine rings. (C) 2013 Elsevier Ltd. All rights reserved.
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