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

Yaylı, Nurettin; Yaşar, Ahmet; Üçüncü, Osman; Sivrikaya, SERPİL; Güleç, Canan; Küçük, Murat; Abbasov, Riza

doi:10.1016/j.jphotochem.2004.11.002

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

Yaylı N., Yaşar A., Üçüncü O., Sivrikaya S., Güleç C., Küçük M., ...Daha Fazla

Journal of Photochemistry and Photobiology A: Chemistry, cilt.171, sa.3, ss.291-298, 2005 (SCI-Expanded, Scopus)

Yayın Türü: Makale / Tam Makale
Cilt numarası: 171 Sayı: 3
Basım Tarihi: 2005
Doi Numarası: 10.1016/j.jphotochem.2004.11.002
Dergi Adı: Journal of Photochemistry and Photobiology A: Chemistry
Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
Sayfa Sayıları: ss.291-298
Açık Arşiv Koleksiyonu: AVESİS Açık Erişim Koleksiyonu
Kocaeli Üniversitesi Adresli: Evet

Özet

Chalconoid-like compounds; (2E,4E)-1,5-diphenylpenta-2,4-diene-1-one (1), (2E,4E)-1-(p-ethyl)phenyl-5-phenylpenta-2,4-diene-1-one (2), (2E,4E)-1-(m-methyl)phenyl-5-phenylpenta-2,4-diene-1-one (3) and (2E,4E)-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 -truxinic-type dimers in solution: rel-(1,2)-dibenzoyl-rel-(3,4)-di-(E)-(2-phenyl)ethenylcyclobutane (5), rel-(1,2)-di-(p-ethyl)-benzoyl-rel-(3,4)-di-(E)-(2- phenyl)ethenylcyclobutane (6), rel-(1,2)-di-(m-methyl)-benzoyl-rel-(3,4)-di-(E)-(2-phenyl)ethenylcyclobutane (7) and rel-(1,2)-di- (p-methyl)-benzoyl-rel-(3,4)-di-(E)-(2-phenyl)ethenylcyclobutane (8), stereoselectively. The possible dimerization products of compound 1 were calculated theoretically. Experimental and theoretical calculations showed that -truxinic-type dimer is the most stable isomer of all. © 2004 Elsevier B.V. All rights reserved. compounds; (2E,4E)-1,5-diphenylpenta-2,4-diene-1-one (1), (2E,4E)-1-(p-ethyl)phenyl-5-phenylpenta-2,4-diene-1-one (2), (2E,4E)-1-(m-methyl)phenyl-5-phenylpenta-2,4-diene-1-one (3) and (2E,4E)-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 -truxinic-type dimers in solution: rel-(1,2)-dibenzoyl-rel-(3,4)-di-(E)-(2-phenyl)ethenylcyclobutane (5), rel-(1,2)-di-(p-ethyl)-benzoyl-rel-(3,4)-di-(E)-(2- phenyl)ethenylcyclobutane (6), rel-(1,2)-di-(m-methyl)-benzoyl-rel-(3,4)-di-(E)-(2-phenyl)ethenylcyclobutane (7) and rel-(1,2)-di- (p-methyl)-benzoyl-rel-(3,4)-di-(E)-(2-phenyl)ethenylcyclobutane (8), stereoselectively. The possible dimerization products of compound 1 were calculated theoretically. Experimental and theoretical calculations showed that -truxinic-type dimer is the most stable isomer of all. © 2004 Elsevier B.V. All rights reserved. compounds; (2E,4E)-1,5-diphenylpenta-2,4-diene-1-one (1), (2E,4E)-1-(p-ethyl)phenyl-5-phenylpenta-2,4-diene-1-one

(2), (2E,4E)-1-(m-methyl)phenyl-5-phenylpenta-2,4-diene-1-one (3) and (2E,4E)-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 ␦-truxinic-type dimers in so-

lution: rel-(1␤,2␣)-dibenzoyl-rel-(3␤,4␣)-di-(E)-(2-phenyl)ethenylcyclobutane (5), rel-(1␤,2␣)-di-(p-ethyl)-benzoyl-rel-(3␤,4␣)-di-(E)-(2-

phenyl)ethenylcyclobutane (6), rel-(1␤,2␣)-di-(m-methyl)-benzoyl-rel-(3␤,4␣)-di-(E)-(2-phenyl)ethenylcyclobutane (7) and rel-(1␤,2␣)-di-

(p-methyl)-benzoyl-rel-(3␤,4␣)-di-(E)-(2-phenyl)ethenylcyclobutane (8), stereoselectively. The possible dimerization products of compound

1were calculated theoretically. Experimental and theoretical calculations showed that ␦-truxinic-type dimer is the most stable isomer of all.

Keywords: Chalconoids; Alnustone; Photodimerizations; Dimers; Theoretical calculat compounds; (2E,4E)-1,5-diphenylpenta-2,4-diene-1-one (1), (2E,4E)-1-(p-ethyl)phenyl-5-phenylpenta-2,4-diene-1-one