By B. J. Wakefield (Auth.)
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Additional resources for The Chemistry of Organolithium Compounds
Example text
3). F o r the sulphur (and selenium) heterocycles, however, rf-orbital participation may be invoked instead of the inductive effect. " An interesting situation arises when there is competition either between a hetero-atom and an ortho-directing substituent, or between two hetero-atoms. Competition between a hetero-atom and a substituent has been particularly studied in the thiophen s e r i e s . N o t unexpectedly, compounds such as 3-methoxy- or 3-methylmercapto-thiophen are metallated largely or exclusively in the 2-position.
When enolisation rather than addition is the desired reaction, bulky, weakly nucleophilic reagents such as triphenylmethyl-lithium are p r e f e r r e d . g. R R - C H L i -C0 Li 2 (refs. 16, 132) (ref. 261) (ref. 241). Once again, the reagents behave as C-lithio-derivatives in their reactions with carbonyl compounds and alkyl halides. M o n o a n i o n s of ketones, generated by the action of reagents such as sodium hydride, may themselves be metallated by organolithium compounds, t o give " d i a n i o n s " .
60), 3 ( ^ . 3 0 ) , Bu Li ( E t 0 ) 3-Methoxyphenanthrene 9-Methoxyphenanthrene 2 2 502 33 n 2 148 148 39 45 210 52 not known 2 9 5 ) , 2(ca. 5) 3(d) n 2 Bu Li (Et 0) n n Anthracene ( C ) 172 269 30 >70 2-Methoxyphenanthrene 2 not known 2 2 l(ca. n n 2 Bu Li (TMEDA) n 2 Bu Li ( E t 0 ) n n n n 4(caA0) 133 79 8 ( 9 1 ) , 2(9) Bu Li ( E t 0 ) 1-Dimethylaminomethylnaphthalene 329, 4 2 9 50-60 ft) 3 n n 2 2-Methoxynaphthalene ( a ) Bu Li (Et 0) Bu Li (TMEDA) B ^ L i (hydrocarbon) 1 -Methoxynaphthalene n 2 l + 2 n Bu Li (THF, E t 0 ) Naphthalene 410 410 Refs.