Synthesis of chalconoid-like compounds and their [2 + 2] photodimerizations in solution and theoretical calculations

Chalconoid-like compounds; (2 E,4 E)-1,5-diphenylpenta-2,4-diene-1-one ( 1), (2 E,4 E)-1-( p-ethyl)phenyl-5-phenylpenta-2,4-diene-1-one ( 2), (2 E,4 E)-1-( m-methyl)phenyl-5-phenylpenta-2,4-diene-1-one ( 3) and (2 E,4 E)-1-( p-methyl)phenyl-5-phenylpenta-2,4-diene-1-one ( 4) have been synthesized an...

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Bibliographic Details
Published in:Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2005-05, Vol.171 (3), p.291-298
Main Authors: Yaylı, Nurettin, Yaşar, Ahmet, Üçüncü, Osman, Sivrikaya, Serpil Ö., Güleç, Canan, Küçük, Murat, Abbasov, Rıza
Format: Article
Language:English
Subjects:
Alnustone
Chalconoids
Dimers
Photodimerizations
Theoretical calculation
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Summary:Chalconoid-like compounds; (2 E,4 E)-1,5-diphenylpenta-2,4-diene-1-one ( 1), (2 E,4 E)-1-( p-ethyl)phenyl-5-phenylpenta-2,4-diene-1-one ( 2), (2 E,4 E)-1-( m-methyl)phenyl-5-phenylpenta-2,4-diene-1-one ( 3) and (2 E,4 E)-1-( p-methyl)phenyl-5-phenylpenta-2,4-diene-1-one ( 4) have been synthesized and their (2 + 2) photosensitized cycloaddition reaction gave four new δ-truxinic-type dimers in solution: rel-(1β,2α)-dibenzoyl-rel-(3β,4α)-di-( E)-(2-phenyl)ethenylcyclobutane ( 5), rel-(1β,2α)-di-( p-ethyl)-benzoyl-rel-(3β,4α)-di-( E)-(2-phenyl)ethenylcyclobutane ( 6), rel-(1β,2α)-di-( m-methyl)-benzoyl-rel-(3β,4α)-di-( E)-(2-phenyl)ethenylcyclobutane ( 7) and rel-(1β,2α)-di-( p-methyl)-benzoyl-rel-(3β,4α)-di-( E)-(2-phenyl)ethenylcyclobutane ( 8), stereoselectively. The possible dimerization products of compound 1 were calculated theoretically. Experimental and theoretical calculations showed that δ-truxinic-type dimer is the most stable isomer of all.
ISSN:1010-6030
1873-2666
DOI:10.1016/j.jphotochem.2004.11.002