Dimesylates
Dimesylates are chemical species that contain two methanesulfonate (mesylate, MsO–) groups. In practice, the term is used for two related classes: bis(methanesulfonate) esters formed when both reactive sites of a diol are converted to mesylate esters, and salts in which a dipositive substrate such as a diamine is paired with two mesylate counterions. The common feature is two MsO– substituents, which are strong leaving groups in nucleophilic substitution reactions.
Preparation typically involves converting a diol to its dismesylate by treating with two equivalents of methanesulfonyl
Reactivity of dimesylates centers on the mesylate groups as excellent leaving groups, enabling sequential substitutions at
Examples include bis(methanesulfonate) derivatives of diols or diamines, sometimes referred to as the dismesylates of the
See also: mesylate, methanesulfonyl chloride, sulfonate esters.