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
Externally publishedYes

Fingerprint

Stereochemistry
Cycloaddition
Silica Gel
Cycloaddition Reaction
Chromatography
Isomers
Gel Chromatography
Irradiation
Light
3-methoxycyclohexenone

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

Cite this

Photo-Cycloaddition of 3-Methoxycyclohexenone and 3-Aminocyclohexenone to Ethoxyethylene : Stereochemistry of the Cycloadducts. / Tsuda, Yoshisuke; Kiuchi, Fumiyuki; Umeda, Ikuno; Iwasa, Etsuo; Sakai, Yuki.

In: Chemical and Pharmaceutical Bulletin, Vol. 34, No. 9, 1986, p. 3614-3622.

Research output: Contribution to journalArticle

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AU - Kiuchi, Fumiyuki

AU - Umeda, Ikuno

AU - Iwasa, Etsuo

AU - Sakai, Yuki

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N2 - 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.

AB - 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.

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