Dioxopyrrolines. LV. Stereochemical pathway of [2 + 2] photocycloaddition reaction of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione to cycloalkadienes and cycloalkenes

T. Sano, H. Enomoto, K. Yasui, Y. Horiguchi, Fumiyuki Kiuchi, Y. Tsuda

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

The photocycloaddition reactions of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione (6) to cycloalkadienes and cycloalkenes were examined. The addition of cyclopentadiene gave the hydroindole 8a (s + a product) as a major product and the cis-fused cyclobutane 7a (s + s product) as a minor one. In contrast, the addition of cyclohexadiene gave the cyclobutane 7b (s + s product) as a major product and the hydroindole 8b (s + a product) as a minor one. The photocycloaddition of cyclopentene, cyclohexene, and indene proceeded predominantly in an s + s manner to give the cis-syn-cis cyclobutanes, 16, 18, and 19, respectively. The stereochemical results were compared with those of the photocycloaddition reactions of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione (1) to the corresponding cyclo-olefins, revealing that the steric relationship of the addends plays an important role in determining the stereochemical pathway of the reaction.

Original languageEnglish
Pages (from-to)846-853
Number of pages8
JournalChemical and Pharmaceutical Bulletin
Volume41
Issue number5
Publication statusPublished - 1993
Externally publishedYes

Fingerprint

Cycloparaffins
Cyclobutanes
Pyrroles
Cyclopentanes
Alkenes

Keywords

  • cyclobutane
  • dioxopyrroline
  • photocycloaddition
  • stereo-s election rule
  • stereochemistry
  • steric effect

ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Dioxopyrrolines. LV. Stereochemical pathway of [2 + 2] photocycloaddition reaction of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione to cycloalkadienes and cycloalkenes. / Sano, T.; Enomoto, H.; Yasui, K.; Horiguchi, Y.; Kiuchi, Fumiyuki; Tsuda, Y.

In: Chemical and Pharmaceutical Bulletin, Vol. 41, No. 5, 1993, p. 846-853.

Research output: Contribution to journalArticle

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T1 - Dioxopyrrolines. LV. Stereochemical pathway of [2 + 2] photocycloaddition reaction of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione to cycloalkadienes and cycloalkenes

AU - Sano, T.

AU - Enomoto, H.

AU - Yasui, K.

AU - Horiguchi, Y.

AU - Kiuchi, Fumiyuki

AU - Tsuda, Y.

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N2 - The photocycloaddition reactions of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione (6) to cycloalkadienes and cycloalkenes were examined. The addition of cyclopentadiene gave the hydroindole 8a (s + a product) as a major product and the cis-fused cyclobutane 7a (s + s product) as a minor one. In contrast, the addition of cyclohexadiene gave the cyclobutane 7b (s + s product) as a major product and the hydroindole 8b (s + a product) as a minor one. The photocycloaddition of cyclopentene, cyclohexene, and indene proceeded predominantly in an s + s manner to give the cis-syn-cis cyclobutanes, 16, 18, and 19, respectively. The stereochemical results were compared with those of the photocycloaddition reactions of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione (1) to the corresponding cyclo-olefins, revealing that the steric relationship of the addends plays an important role in determining the stereochemical pathway of the reaction.

AB - The photocycloaddition reactions of 4,5-diethoxycarbonyl-1H-pyrrole-2,3-dione (6) to cycloalkadienes and cycloalkenes were examined. The addition of cyclopentadiene gave the hydroindole 8a (s + a product) as a major product and the cis-fused cyclobutane 7a (s + s product) as a minor one. In contrast, the addition of cyclohexadiene gave the cyclobutane 7b (s + s product) as a major product and the hydroindole 8b (s + a product) as a minor one. The photocycloaddition of cyclopentene, cyclohexene, and indene proceeded predominantly in an s + s manner to give the cis-syn-cis cyclobutanes, 16, 18, and 19, respectively. The stereochemical results were compared with those of the photocycloaddition reactions of 4-ethoxycarbonyl-5-phenyl-1H-pyrrole-2,3-dione (1) to the corresponding cyclo-olefins, revealing that the steric relationship of the addends plays an important role in determining the stereochemical pathway of the reaction.

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