Kinetics, Products, and Mechanisms of Reaction of tert-Butyl Chloride with Sodium Methoxide in Methanol and Dimethyl Sulfoxide/Methanol Solvents

Article abstract of DOI:10.1021/jo00274a014

The rate of reaction of tert-butyl chloride with methanolic sodium methoxide shows little variation with base concentration up to 1 mol/L, but the presence of MeONa causes the product composition to shift strongly toward 2-methylpropene.What mechanisms prevail is uncertain; one possibility is that as increases the E2 mechanism participates to a small but increasing extent while E1-S_N1 solvolysis continues at a nearly constant rate.When the solvent is enriched in dimethyl sulfoxide, the overall rate increases robustly with in nonlinear fashion, with increasing slope, and the product is almost entirely the alkene.