Browsing Center for Student Research and Creativity by Author "Jessica Stanfield"
Convenient Parallel Synthesis of Alkyl- and Aryl-S-tert-Butyl ThiothersRebecca Norcross; Jessica Stanfield; Richard W. Fitch (2012-05-21)While preparing novel cysteine derivatives as oxidation catalysts, we needed S-tert-butylcysteine. We also examined acid-promoted tert-butylation of thiols using tert-butanol as reagent and solvent. While cysteine and aminoethanethiol work well using tBuOH in 4M HCl, other thiols fail in the aqueous environment and aerobic conditions. We examined a variety of aliphatic and aromatic thiols in tBuOH with H2SO4 catalysis and found that argon sparging and the use of 1 eq of acid led to good yields in a parallel format.