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

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

研究成果: Article

3 引用 (Scopus)

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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.

元の言語English
ページ(範囲)3614-3622
ページ数9
ジャーナルChemical and Pharmaceutical Bulletin
34
発行部数9
DOI
出版物ステータスPublished - 1986 1 1
外部発表Yes

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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