4,5,6,7-Tetrachloro-3-(furan-3-yl)-3-hydroxy-2-(3-hydroxypropyl)-2,3-dihydro-1<i>H</i>-isoindol-1-one

Fun, Hoong‐Kun; Chantrapromma, Suchada; Shen, Yong‐Miao; Xu, Jie

doi:10.1107/s1600536807013736

Cited by 2 publications

(3 citation statements)

References 4 publications

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“…Bond lengths and angles are in normal ranges (Allen et al, 1987) and are comparable to those in a related structure (Fun et al, 2007). The isoindole unit (C1-C8/N1) is essentially planar, with a maximum deviation of 0.066 2…”

Section: S1 Commentmentioning

confidence: 58%

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4,5,6,7-Tetrachloro-3-(cyclohepta-1,3,6-trien-1-yl)-3-hydroxy-2-(2-hydroxyethyl)-2,3-dihydro-1H-isoindol-1-one

et al. 2007

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Key indicators: single-crystal X-ray study; T = 100 K; mean (C-C) = 0.003 Å; disorder in main residue; R factor = 0.047; wR factor = 0.130; data-to-parameter ratio = 18.3.In the title compound, C 17 H 13 Cl 4 NO 3 , the isoindole unit is essentially planar. The seven-membered ring adopts a boat conformation. The O atom of the hydroxyethyl group is disordered over two positions with essentially equal occupancies. In the crystal structure, the molecules are linked by O-HÁ Á ÁO and O-HÁ Á ÁCl hydrogen bonds into a two-dimensional network parallel to the (010) plane.

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Section: S1 Commentmentioning

confidence: 58%

“…For bond-length data, see: Allen et al (1987). For related literature, see: Evans & Holmes (1991); Griesbeck et al (1996); Illuminati & Mandolini (1981); Xue et al (2000); Fun et al (2007). Mo K radiation = 0.73 mm À1 T = 100.0 (1) K 0.45 Â 0.12 Â 0.10 mm…”

Section: Related Literaturementioning

confidence: 99%

4,5,6,7-Tetrachloro-3-(cyclohepta-1,3,6-trien-1-yl)-3-hydroxy-2-(2-hydroxyethyl)-2,3-dihydro-1H-isoindol-1-one

et al. 2007

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“…[31] The crystal structure of 17 is shown in Figure 5. Control experiments showed that, both 17 and 18 are photostable, and photolysis of either 17 or 18 in benzene caused no appreciable decomposition.…”

Section: à3mentioning

confidence: 99%

Intermolecular Photocyclizations of N‐(ω‐Hydroxyalkyl)tetrachlorophthalimide with Alkenes Leading to Medium‐ and Large‐Ring Heterocycles—Reaction Modes and Regio‐ and Stereoselectivity of the 1,n‐Biradicals

Shen

Yang

Chen

et al. 2010

Chemistry A European J

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A new photocyclization strategy by using intermolecular tandem reactions between N-(omega-hydroxyalkyl)-4,5,6,7-tetrachlorophthalimides (1, 2, and 3) and a series of acyclic and cyclic alkenes is reported. Electron transfer of the triplet-excited phthalimide with the alkene and regioselective trapping of the alkene cation radical by the hydroxyl group at the phthalimide side chain gives a triplet 1,n-biradical, which after intersystem crossing (ISC) leads to regio- and diastereoselective synthesis of polycyclic heterocycles with an N,O-containing medium to large ring. Regio- and diastereoselectivity in the cyclizations are clarified by unambiguous steric structure assignments of the products by X-ray diffraction or extensive 2D NMR measurements. The diastereoselectivity is decided by the stereochemical course of the ISC process of the triplet 1,n-biradicals. These intermolecular photoreactions also furnish a new strategy to generate triplet 1,n-biradicals. Therefore, in photoreactions of 1 and 2 with phenylcyclohexene, the unprecedented stereoselective formation of products by intramolecular hydrogen-atom transfer in the 1,n-biradical intermediate was found (9 and 23). These facts provide direct verification to the reaction pathways of the 1,n-biradicals and give a new insight into the factors deciding reaction-pathway partitioning and stereoselectivity.

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4,5,6,7-Tetrachloro-3-(furan-3-yl)-3-hydroxy-2-(3-hydroxypropyl)-2,3-dihydro-1H-isoindol-1-one

Cited by 2 publications

References 4 publications

4,5,6,7-Tetrachloro-3-(cyclohepta-1,3,6-trien-1-yl)-3-hydroxy-2-(2-hydroxyethyl)-2,3-dihydro-1H-isoindol-1-one

4,5,6,7-Tetrachloro-3-(cyclohepta-1,3,6-trien-1-yl)-3-hydroxy-2-(2-hydroxyethyl)-2,3-dihydro-1H-isoindol-1-one

Intermolecular Photocyclizations of N‐(ω‐Hydroxyalkyl)tetrachlorophthalimide with Alkenes Leading to Medium‐ and Large‐Ring Heterocycles—Reaction Modes and Regio‐ and Stereoselectivity of the 1,n‐Biradicals

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