By B. J. Wakefield (Auth.)
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Extra info for The Chemistry of Organolithium Compounds
3*8°. Small a m o u n t s o f other products also formed. Five products from dimetallation also obtained. 96% R,R + 4 % R,S. Product had ca. 6 7 % optical p u r i t y . Other products also formed. Prolonged reaction leads to (2-butyl-2-pyridyl) ferrocene as m a i n product. Plus trace monosubstituted. Mixture o f deuterated products obtained o n hydrolysis with D 0 . T h e l,r-disubstituted product predominated even in the early stages of the reaction. Total yield ca. 7 8 % . W i t h an excess o f the reagent, polylithiation o c c u r s .
Ring-metallation is observed in several instances where the organolithium compound also reacts with the substituent. In some cases an excess of the reagent leads to normal or/Atf-metallation; examples are aniline, phenol, and iV-monosubstituted benzamides (see Table 3 . 5 . ) . With thioanisole metallation occurs mainly in the ring, b u t the metal then migrates to the side c h a i n . On the other hand, the a-metallation of toluene apparently takes place directly, rather than by migration from the r i n g / (384b) (145) (145) (176) (50) (414) 5 0 , 6 8 ) Preparation by Metallation 41 F o r the reaction between organolithium compounds a n d halogenobenzenes, alkylation (see Chapter 10) a n d metal-halogen exchange (see Chapter 4) are alternative reactions to metallation.
275. ( 2 7 5 2 7 5 a ) CHCI3 T H ^ ^ C C l L i - S a . ( C C l ) H g 3 3 2 > 90% t Hexamethylphosphorotriamide, (Me N) PO. 2 3 (refs. CCl H B TH 2 U F °1;' . 228) 70% /C0 H AA Ar C=CHCl 2 T H F ,_ B u 4 2 tori^Ar2C^c( n L 5 <§S£ A r C = c ( (refs. 286-7) 2 u p to 9 7 % CF =CFH 2 _ E t i 0 jo 1 0 ) -^gf^ CF -CFLi 2 CF —CF. C(CF ) . OH 63% 2 3 2 (ref. 101) While such reactions have considerable scope, complications may arise from competing metal-halogen exchange (see Chapter 4). F o r example, the reaction of bromochloromethane with n-butyl-lithium in T r a p p mixture " at — 110° gives a mixture of bromochloromethyl-lithium (via metallation) and chloromethyl-lithium (via metal-halogen exchange).
The Chemistry of Organolithium Compounds by B. J. Wakefield (Auth.)