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

Vladimir Lokshin (1) , Vladimir Khodorkovsky (1)

1 CINaM - Centre Interdisciplinaire de Nanoscience de Marseille

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.

Mots clés: 1 3-indandione; spiro-1-3-diketone; photochemistry; photochromism; photoacids

Domaines: Chimie organique

Vladimir Lokshin, Vladimir Khodorkovsky. Stereochemistry in control of photochemical reactivity: 2,6-Diaryl-4H-spiro[cyclohexane-1,2′-indene]-1′,3′,4-triones. Tetrahedron, 2018, 74 (3), pp.418-424. ⟨10.1016/j.tet.2017.12.014⟩. ⟨hal-03500756⟩