Tetrabutylammonium fluoride promoted regiospecific reactions of trimethylsilyl-o-carborane with aldehydes

Chemistry Letters

Volumn , Issue 9, 1996, Pages 791-792

  Cai, Jianping ^d   Nemoto, Hisao ^d   Nakamura, Hiroyuki ^a   Singaram, Bakthan ^b   Yamamoto, Yoshinori ^c  

^a KYUSHU UNIVERSITY   (Japan)

^b UNIVERSITY OF CALIFORNIA   (United States)

^c TOHOKU UNIVERSITY   (Japan)

^d INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0030353396     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1996.791     Document Type: Article

References (16)

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14. The preparation of trimethylsilyl-o-carborane 1 is as follows;
15. -3 solution of n-BuLi in hexane (3.13 ml, 5 mmol) dropwise with stirring. The mixture was allowed to stir for 30 min at -78 °C and trimethylsilyl chloride was added dropwise. The solution was stirred for 1 h and then warned to ambient temperature. The reaction was quenched with water, extracted with ether, and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by short column chromatography on silica gel with hexane as eluent, which afforded 1 as a while solid in 86% yield (0.93 g, 4.3 mmol). In this case, di-trimethylsilyl substituted carborane was not obtained. The use of diluted solution of lithium carborane is essential to obtain the mono-silyl substituted carborane derivative.
16. -3, 1 ml) was added at 25 °C and stirred for 1h. The reaction mixture was diluted with ether (20 ml), washed with water (2x5 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was purified by column chromatography [silica gel, hexane-ethyl acetate (2:1) as eluent] to afford essentially pure 1-(o-carboranyl)-4′-cyanobenzyl alcohol (0.23 g, 82%).