Unexpected formation of fluorine-containing multiply substituted dispirocyclohexanes from the reaction of ethyl-4,4,4-trifluoro-1,3- dioxobutanoate and 2-arylideneindane-1,3-diones

Synlett

Volumn , Issue 11, 2009, Pages 1842-1846

  Dai, Baifan ^a   Song, Liping ^a,b   Wang, Pengyuan ^a   Yi, Hai ^a   Cao, Weiguo ^a   Jin, Guifang ^b   Zhu, Shizheng ^b   Shao, Min ^a  

^a SHANGHAI UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

2 arylidene indan 1,3 dione; Ethyl 4,4,4 trifluoro 3 oxobutanoate; Fluorine containing; Polysubstitution; Spiro compound

Indexed keywords

1,3 INDANDIONE DERIVATIVE; 2 ARYLIDENEINDANE 1,3 DIONE DERIVATIVE; BUTYRIC ACID; CYCLOHEXANE DERIVATIVE; DISPIROCYCLOHEXANE DERIVATIVE; ETHYL 4,4,4 TRIFLUORO 1,3 DIOXOBUTANOATE; FLUORINE; PIPERIDINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; REACTION ANALYSIS; SPECTROSCOPY; X RAY DIFFRACTION;

EID: 67650146390     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217361     Document Type: Article

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61. A Typical Experimental Procedure for the Preparation of 5a To a mixture of ethyl 4,4,4-trifluoro-3-oxobutanoate (184.0 mg, 1.0 mmol) and 2-benzylidene-indane-1,3-dione (468.0 mg, 2.0 mmol) in MeCN (3.0 mL) was added a catalytic amount of pipreridine (8.5 mg, 0.1 mmol). The resulting mixture was stirred at r.t. until the reaction was completed (8 h, monitored by TLC). The solvent was removed under reduced pressure. And then the residue was purified by column chromatography on silica gel using PE-EtOAc [6:1 (v/v)] as eluent to afford 5a as a colorless solid in 78% yield.
62. 3)
63. 1H NMR spectrum showed broad signals due to decreased rotational flexibility of the highly puckered structures.
64. CCDC 720376 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data- request/cif, or by emailing data-request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 (1223)336033.