Abstract

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)]

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