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


YAYLI N. , YASAR A. , UCUNCU O. , SIVRIKAYA S., GUIEC C., Kucuk M. , ...Daha Fazla

JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, cilt.171, ss.291-298, 2005 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 171 Konu: 3
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1016/j.jphotochem.2004.11.002
  • Dergi Adı: JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY
  • Sayfa Sayıları: ss.291-298

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