Archive for May 8th, 2013

Transition states for the (base) catalysed ring opening of propene epoxide.

Wednesday, May 8th, 2013

The previous post described how the acid catalysed ring opening of propene epoxide by an alcohol (methanol) is preceded by pre-protonation of the epoxide oxygen to form a “hidden intermediate” on the concerted intrinsic reaction pathway to ring opening. Here I take a look at the mechanism where a strong base is present, modelled by tetramethyl ammonium methoxide (R4N+.OMe), for the two isomers R=Me; R’=Me, R”=H and R’=H, R”=Me.

(more…)