H. Walborsky, M. P. Murari
Nov 1, 1984
Citations
0
Influential Citations
5
Citations
Journal
Canadian Journal of Chemistry
Abstract
The 1,3-elimination of methoxide by carbanions generated from the reaction of (±)-1,3-dimethoxy-1,1-diphenylbutane with the alkali metals, lithium, sodium, and potassium, in various solvents was studied to determine the significance of cation–methoxyl coordination due to decreasing charge/radius ratio of the cations and also the cation complexing ability of the solvent. The stereochemistry of cyclization in the reaction of (S)-(−)-1,3-dimethoxy-1,1-diphenylbutane with lithium metal in tetrahydrofuran and with sodium metal in methylcyclohexane to yield 1-methyl-2,2-diphenylcyclopropane was determined. The reaction proceeded by an intramolecular SN2-type displacement to yield optically pure product of inverted configuration.