Photo-Cycloaddition of 3-Methoxycyclohexenone and 3-Aminocyclohexenone to Ethoxyethylene: Stereochemistry of the Cycloadducts

Yoshisuke Tsuda, Fumiyuki Kiuchi, Ikuno Umeda, Etsuo Iwasa, Yuki Sakai

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

Irradiation of a methanolic solution of 3-methoxycyclohexenone and ethoxyethylene with 254 nm light gave four stereoisomeric head-to-tail [2 + 2] cycloadducts in the ratios indicated in Fig. 3. The structure and stereochemistry of all the isomers were determined by chemical correlations and spectroscopic means, respectively. The time-course product analysis suggested that, in this reaction, the exo and endo oriented π-complexes are equally formed, and both give the cycloadducts with a slight preference for antara-selectivity. The analogous cycloadduct of 3-aminocyclohexenone to ethoxyethylene decomposed into 2-ethoxycyclooctane-l,5-dione on silica gel chromatography.

Original languageEnglish
Pages (from-to)3614-3622
Number of pages9
JournalChemical and Pharmaceutical Bulletin
Volume34
Issue number9
DOIs
Publication statusPublished - 1986 Jan 1

Keywords

  • 2 + 2 adduct
  • 2D NMR
  • 3-aminocy-clohexenone
  • 3-methoxycyclohexenone
  • acyclic olefin
  • bicyclo[4.2.0]octanone
  • cyclooctanedione
  • photo-cycloaddition
  • stereochemistry
  • time-course product analysis

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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