Mustard Carbonate Analogues: Influence of the Leaving Group on the Neighboring Effect

The substitution of a chlorine atom with a carbonate moiety in mustard compounds has led to a new class of molecules, namely, mustard carbonates that retain the reactivity of the well-know toxic iprites but are safe for the operator and the environment. In this paper, for the first time, the influence of the leaving group on the anchimeric effect of sulfur mustard carbonates has been investigated both in autoclave and neat conditions. Results have led to an enhanced selectivity of the anchimerically driven alkylation, as well as to improved and more accessible reaction conditions.