A New Synthesis of Neopentyl 2,4,6-Tri-t-butylphenyl Ether and Related Hindered Ethers

The SN reactions of neopentyl, (1-adamantyl)methyl, and related substrates with potassium 2,4,6-tri-t-butylphenoxide gave the corresponding highly hindered ethers in moderate yields. They were neopentyl and (1-adamantyl)methyl 2,4,6-tri-t-butylphenyl ethers, and 1,3-bis(2,4,6-tri-t-butylphenoxy)-2,2-dimethylpropane. The kinetics for these reactions suggest the SN2 mechanism.