Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent

Robertson, Stuart D. and Kennedy, Alan R. and Liggat, John J. and Mulvey, Robert E. (2015) Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent. Chemical Communications, 51 (25). pp. 5452-5455. ISSN 1359-7345

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    Abstract

    1-lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-) butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media.