Solutions of lithiated cumulenic ethers and bis‐ethers R2CHCCC(Li)OR3 and R1OCHCCC(Li)OR3 can be obtained by treatment of the compounds R1OCH(R)2)CCCH2OR3 and R1OCH2CCCH(OR3)2 respectively with 2 equivalents of butyllithium in ether. Reaction of these solutions with H2O, D2O, methyl iodide, α‐chloro‐ethers or ketones gives the cumulenic compounds or their derivatives in good yields. Solutions of lithiated cumulenic thioethers R2CHCCC(Li)SR3 are obtained in an analogous way, but hydrolysis affords the isomeric enynic thioethers R2CHCHCCSR3 in addition to the expected cumulenic thioethers R2CHCCCHSR3. Elimination of R1OH from R1OC(R2)2CCCH(SR3)2 with 1 equivalent of C4H9Li leads to the cumulenic dithioacetals (R2)2CCCC(SR3)2.
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MANTIONE et al. (1970) studied this question.
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