Remote functionalisation via sodium alkylamidozincate intermediates : access to unusual fluorenone and pyridyl ketone reactivity patterns
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
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Abstract
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.
Creators(s): |
Crawford, James J., Fleming, Ben J. ![]() ![]() | Item type: | Article |
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ID code: | 33243 |
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: | 26 Feb 2021 04:49 |
URI: | https://strathprints.strath.ac.uk/id/eprint/33243 |
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