Allenation of Carbonyl Compounds with Alkenyltitanocene Derivatives

Journal of Organic Chemistry

Volumn 62, Issue 4, 1997, Pages 782-783

  Petasis, Nicos A ^a   Hu, Yong Han ^a  

^a UNIVERSITY OF SOUTHERN CALIFORNIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000319120     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9620876     Document Type: Article

References (30)

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22. Typical procedure (Table 1, entry 2): To a solution of titanocene dichloride (500 mg, 2.0 mmol) in THF (20 mL) stirred at -40 °C under nitrogen was added dropwise 1-propenylmagnesium bromide (8.03 mL, 0.5 M solution in THF, 4.0 mmol). After the mixture was warmed to 0 °C over 1.5 h, acetophenone (0.117 mL, 1.0 mmol) was added, and stirring was continued at rt monitored by TLC. Concentration of the solution (to 1 mL), dilution with hexane (30 mL), removal of the titanocene byproduct by filtration, solvent evaporation, and flash column chromatography (silica, hexane) gave the allene product (120 mg, 83%).
23. All products gave satisfactory spectroscopic and analytical data.
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