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

被引：3

作者：

Lokshin, Vladimir ^{[1
]}

Khodorkovsky, Vladimir ^{[1
]}

机构：

[1] Aix Marseille Univ, CNRS, CINaM UMR 7325, F-13288 Marseille, France

来源：

TETRAHEDRON | 2018年 / 74卷 / 03期

关键词：

1,3-Indandione; Spiro-1,3-diketone; Photochemistry; Photochromism; Photoacids; EN ALCOYLIDENE-PHTALIDES; STEREOSELECTIVE-SYNTHESIS; ORGANOCATALYTIC SYNTHESIS; ASYMMETRIC-SYNTHESIS; ANNULATION STRATEGY; ISOMERIZATION; DERIVATIVES; CASCADE; 2-ARYLIDENEINDANE-1,3-DIONES; CYCLOADDITION;

D O I：

10.1016/j.tet.2017.12.014

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：418 / 424

页数：7

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