75624-90-7Relevant academic research and scientific papers
Vinyl ether hydrolysis. XIV. Methyl β,β-di-tert-butylvinyl ether: buttressing steric effects
Chiang, Y.,Kresge, A. J.,Tidwell, T. T.,Walsh, P. A.
, p. 2203 - 2206 (2007/10/02)
The highly congested molecule, methyl β,β-di-tert-butylvinyl ether, undergoes reaction in dilute aqueous mineral acid solutions by a normal vinyl ether hydrolysis mechanism and gives an unrearranged aldehyde product.The tert-butyl groups retard the rate of hydrolysis, but the effect of cis and trans substituents is not cumulative; this is attributed to a repulsive nonbonded interaction, relieved in the course of rection, between the ether oxygen atom and the cis-tert-butyl group buttressed by the trans-tert-butyl group.
