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. , ...More

Journal of Photochemistry and Photobiology A: Chemistry, vol.171, no.3, pp.291-298, 2005 (Journal Indexed in SCI Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 171 Issue: 3
  • Publication Date: 2005
  • Doi Number: 10.1016/j.jphotochem.2004.11.002
  • Title of Journal : Journal of Photochemistry and Photobiology A: Chemistry
  • Page Numbers: pp.291-298
  • Keywords: Alnustone, Chalconoids, Dimers, Photodimerizations, Theoretical calculation

Abstract

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 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. © 2004 Elsevier B.V. All rights reserved.