A range of compounds has been successfully converted to thiols and related derivatives for evaluation as medical counter-measures to mustard exposure. One class of compounds of special interest possesses the -S-S-CO2R functional group since they can undergo rather facile hydrolysis to (re)generate a free thiol, R'-S-S-CO2R -› R'-SH. Such disulfides also are of interest since they can be converted to a seemingly limitless variety of disulfides, R'-S-S-R. A second type of disulfide that has proven useful in this program involves those derived from 2-mercaptobenzothiazole, BT-SH. Disulfides of the type R-S-S-BT are quite stable and odor free. They, like R'-S-S-CO2R, can be converted in excellent yields to molecules of the type R-S-S-R'. During this program we have produce a wide range of structures for evaluation including those containing carbohydrate fragments, amino acid fragments, di- and tripeptide fragments and sterols. Using these approaches we have begun to prepare structures that contain both hydroxyl groups (-OH) and mercapto groups (-SH). We also have demonstrated that such thiols can be converted to stable metal salts/complexes, including those derived from zinc. Some of the target compounds have been evaluated as anti-vesicants and several exhibit activity.