Crawford, James J. and Fleming, Ben J. and Kennedy, Alan R. and Klett, Jan and O'Hara, Charles T. and Orr, Samantha A. (2011) Remote functionalisation via sodium alkylamidozincate intermediates : access to unusual fluorenone and pyridyl ketone reactivity patterns. Chemical Communications (London), 47 (13). pp. 3772-3774. ISSN 0009-241X
c1cc10193e.pdf - Published Version
Available under License Unspecified.
Download (1MB) | Preview
Treating fluorenone or 2-benzoylpyridine with the sodium zincate [(TMEDA)center dot Na(mu-Bu-t)(mu-TMP)Zn(Bu-t)] in hexane solution, gives efficient Bu-t addition across the respective organic substrate in a highly unusual 1,6-fashion, producing isolable organometallic intermediates which can be quenched and aerobically oxidised to give 3-tert-butyl-9H-fluoren-9-one and 2-benzoyl-5-tert-butylpyridine respectively.
|Keywords:||metal-mediated zincation, ferroelectric liquid-crystals, directed ortho-metalation, tertiary aromatic amide, structural insights, polar order, 1,4-dihydropyridines, magnesiation, derivatives, complexes, Chemistry, Chemistry(all)|
|Subjects:||Science > Chemistry|
|Department:||Faculty of Science > Pure and Applied Chemistry|
|Depositing user:||Pure Administrator|
|Date Deposited:||14 Sep 2011 15:09|
|Last modified:||04 May 2016 19:29|