beta-Heterosubstituted lithium alkyls and alkenyls

The appropriate b-hetero-substituted alkyl and alkenyl iodide in 2:2:1:1 methylal-tetrahydrofuran-Et2O-pentane at -130 Deg with BuLi yielded by iodine-Li exchange the corresponding Li derivs. which were characterized by carboxylation and subsequent esterification of the resulting acids with CH2N2. In this manner were prepd. solns. of the following Li derivs. (% yield of Me ester given): cis-ClCH:CHLi, 0.2; ClCH2CH2Li, 5.0; FCH2CH2Li, 8.0; MeOCH2CH2Li, 5.3; I, 42. I rearranged at -50 Deg to II. I and II carboxylated and treated with CH2N2 yielded the corresponding Me esters, m. 86-8 and 63-5 Deg resp. The hydrolysis of I and II gave cryst. (m. 38-40 Deg) and liquid chlorinated hydrocarbon, resp. [on SciFinder (R)]

Published in:
Angewandte Chemie, International Edition, 5, 5, 519
CAN 65:29515 39 Organometallic and Organometalloidal Compounds Univ. Heidelberg,Germany. Journal written in English. 540-67-0 (Ether, ethyl methyl) (lithium deriv.); 6591-37-3 (Lithium, (2-fluoroethyl)-); 6591-38-4 (Lithium, (2-chloroethyl)-); 6591-40-8 (Lithium, (1,2,3,4-tetrachlorotricyclo[,6]hept-3-yl)-); 6720-90-7 (Lithium, (2-methoxyethyl)-); 92502-84-6 (Lithium, (1,4,5,6-tetrachloro-5-norbornen-2-yl)-) (prepn. of)

 Record created 2006-03-03, last modified 2018-01-27

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