Journal of the American Chemical Society p. 6712 - 6716 (1981)
Update date:2022-07-30
Topics:
Caserio, Marjorie C.
Souma, Yoshie
Kim, Jhong K.
As a test of stereoelectronic control in the gas phase, the rates of ionic cleavage of the exocyclic methoxyl group of 2-methoxy-cis-4,6-dimethyl-1,3-dioxane diastereomers have been measured by ion cyclotron resonance techniques.The reactant ions were isopropyl and (methylthio)methyl cations derived from electron impact cleavage of 2-methylpropane and 2-(methylthio)ethanol, respectively.Within experimental error, the rates of cleavage of the equatorial methoxyl were the same as those of the axial methoxyl with a given reactant ion.With use of mixtures of deuterium-labeled and unlabeled diastereomers and reactant ions derived from isopropyl ether and acetylacetone, a slight (10percent) preference was seen for cleavage of the axial methoxyl group.The significance of these results in terms of stereoelectronic and conformational effects is discussed.
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