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A series of esters of dithiobutyric acid was prepared using the carbodiimide coupling system. These esters were used to examine the kinetic feasibility of release of alcohols by reductive cleavage of the disulfide. Release of p-nitrophenol was rapid following reduction with dithiothreitol at pH ~10.5. Intramolecular thiolysis is at least one hundred-fold faster then base hydrolysis at this pH. NMR experiments established rapid alcohol release for phenolates and ethanolamine derivatives but alkyl substrates were found to release slowly. Self-assembled monolayers (SAMs) formed from nitrophenol or ethanolamine derivatives produce the expected quantity of alcohol following reductive release from gold powder.

Intramolecular thiolysis of 4-mercaptobutyrate esters: developing a “traceless” linker for alcohol release from self-assembled monolayers on gold