CHEMISTRY OF CARBANIONS .16. STEREOCHEMISTRY OF ALKYLATION OF 1-ACETYL AND 1-CYANO DERIVATIVES OF 4-(T-BUTYL)CYCLOHEXANE

The lithium enolate anions 1 and 26 from methyl 4-t-butyIcyclohexyl ketone (9) and l-cyano-4-t-butylcyclohexane (21) were alkylated with methyl iodide in 1,2-dimethoxyethane solution. In each case, the major monoalkylated product was the material containing an equatorial methyl group. These results are discussed in light of earlier N-methylation of 1-ethyl-4-t-butylpiperidine (4) to form a mixture of salts in which the stereoisomer with an axial methyl group predominated. © 1968, American Chemical Society. All rights reserved.