Organolithium routes to 1,2-disubstituted ethylene derivatives. An attempted synthesis of 1,2-dilithioethylene

Add time:07/21/2019    Source:sciencedirect.com

The attempted preparation of trans-1,2-dilithioethylene by the action of two molar equivalents of n-butyllithium on trans-1,2-bis(tri-n-butystannyl) ethylene was unsuccessful, the reaction stopping at the Bu3SnCHCHLi + BuLi stage. However, trans-1,2-disubstituted ethylene derivatives could be prepared in good yield by a stepwise sequence in a one-pot process. Thus, trans-Bu3SnCHCHSnBu3 was treated successively with molar equivalents of n-Buli, Me3SiCl n-Buli and Me2CO to give trans-Me3SiCHCHCMe2OH in 63% yield. Prepared in similar fashion were trans-Me3SiCHCHSiMe3 trans-Me3SiCHCHSnMe3 and trans-Me3SiCHCHCH3. These products, as well as (trans-Me3SiCHCH)2Hg, also were prepared by appropriate reactions of trans-Me3SiCHCHLi, which was obtained by the transmetalation reaction of phenyllithium with trans-Me3SiCHCHSnPh3 in diethyl ether solution. The (Ph3P)4Pd-catalyzed demercuration of trans-Me3SiCHCH)2Hg gave trans,trans-Me3SiCHCHCHCHSiMe3 in 95% yield.

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