Synthesis and crystal structure of 1,2,4-trifluoro-3,5,6- tris(triisopropylsilyl)benzene

Tetrahedron Letters

Volumn 47, Issue 4, 2006, Pages 493-495

  Hanamoto, Takeshi ^a   Koga, Yukinori ^a   Kawanami, Toshio ^b   Furuno, Hiroshi ^b   Inanaga, Junji ^b  

^a SAGA UNIVERSITY   (Japan)

^b KYUSHU UNIVERSITY   (Japan)

Author keywords

Crowded benzene; Dewar benzene; Fluorinated compound; Isomerization; X ray structure

Indexed keywords

1,2,4 TRIFLUORO 3,5,6 TRIS(TRIISOPROPYLSILYL)BENZENE; ACETYLENE DERIVATIVE; BENZENE DERIVATIVE; BICYCLO COMPOUND; FLUORINE DERIVATIVE; FLUORO(TRIISOPROPYLSILYL)ACETYLENE; FLUOROBENZENE; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; FLUORINATION; PHOTOCHEMISTRY; SYNTHESIS; THERMODYNAMICS; X RAY CRYSTALLOGRAPHY;

TRIFLUORO;

EID: 29144433982     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.11.055     Document Type: Article

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14. Isomerization of 1 under thermal conditions: Dewar benzene 1 (60.0 mg, 0.10 mmol) is placed in a flask, which is kept for 45 min at 220°C with a glass tube oven under argon atmosphere. After cooling to a room temperature, the resulting pale green mixture was purified by silica gel chromatography (hexane) to afford 55.2 mg (93%) of 2.
15. Isomerization of 1 under irradiation conditions: A degassed hexane solution (10 mL) containing Dewar benzene 1 (61.1 mg, 0.10 mmol) in a quartz test tube was irradiated (λ >254 nm) for 8 h at 40°C. Concentration of the reaction mixture afforded 60.9 mg (quant) of 2.
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17. 15). All hydrogen atoms were positioned geometrically and refined as riding. CCDC-279251 contains the supplementary crystallographic data for this letter. These data can be obtained free of charge via www.ccdc.cam.ac.uk/const/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax (+44) 1223-336-033; or deposit@ccdc.cam.ac/uk ).
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