An intramolecular acyl transfer reaction limited by substrate isomerization
Abstract
The bell-shaped pH–rate profile for the rearrangement of S-benzoyl-1,1,3-trimethylisothiouronium bromide to 1-benzoyl-1,3,3-trimethylthiourea has been interpreted in terms of a rate-determining syn–anti-isomerization of the sterically favoured but inert species HA ⇌ A to the reactive species HA′⇌ A′.