851-06-9

Bis[n-(p-toluenesulfonyl)]sulfodiimide can act as an enophile in ene reactions and as a dienophile in Diels-Alder reactions; participates in [2 + 2] and [3 + 2] cycloaddition reactions; cycloadds to ynamines.

A convenient in situ method for the synthesis of bis[N-(p-toluenesulfonyl)]sulfodiimide is by treating N-Sulfinyl-p-toluenesulfonamide with dry Pyridine in benzene (eq 1). An alternative procedure is the reaction of SCl2 or S2Cl2 with p-toluenesulfonamide in the presence of a base such as pyridine or triethylamine (eq 2).

Extremely sensitive to moisture and should be stored in a desiccator  and handled only in a dry box or glove bag. Typically the title compound is generated and used in situ.