Stereochemistry in control of photochemical reactivity: 2,6-Diaryl-4H-spiro[cyclohexane-1,2′-indene]-1′,3′,4-triones

Vladimir Lokshin, Vladimir Khodorkovsky

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

Abstract

Photochemical reaction of trans-2,6-diaryl-4H-spiro[cyclohexane-1,2′-indene]-1′,3′,4-triones gives rise to the formation of the ylidenephthalide derivatives as previously observed for 2,2-disubstituted 1,3-indandiones. In contrast, the respective cis-isomers afford different products originating from the unprecedented reversible cyclohexanone cycle breaking (photo-induced retro-Michael reaction). The difference between the reaction pathways does not depend on the irradiation wavelengths or the light source power and is observed both in solution and solid state.

Original languageEnglish
Pages (from-to)418-424
Number of pages7
JournalTetrahedron
Volume74
Issue number3
DOIs
StatePublished - 18 Jan 2018
Externally publishedYes

Keywords

  • 1,3-Indandione
  • Photoacids
  • Photochemistry
  • Photochromism
  • Spiro-1,3-diketone

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Stereochemistry in control of photochemical reactivity: 2,6-Diaryl-4H-spiro[cyclohexane-1,2′-indene]-1′,3′,4-triones'. Together they form a unique fingerprint.

Cite this