Disulfides. 1. Syntheses Using 2,2'-Dithiobis(benzothiazole)

Article abstract of DOI:10.1021/jo00105a048

2,2'-Dithiobis(benzothiazole) produces unsymmetric disulfides containing the 2-benzothiazolyl fragment in both high yield and purity when reacted with 1 equiv of a variety of alkane and arene thiols under mild conditions.In turn, these unsymmetric disulfides react with a variety of thiols to produce either symmetric disulfides or new unsymmetric disulfides in excellent yields.At room temperature, 2 equiv of most thiols are oxidized essentially quantitatively to the corresponding symmetric disulfide by 2,2'-dithiobis(benzothiazole).Thiols employed at various stages include 1-propanethiol, 2-propanethiol, 2-methyl-2-propanethiol, phenylmethanethiol, 2-mercaptoethanol, 2-mercaptoethylamine (MEA) hydrochloride, 2-methoxybenzenethiol, 4-methoxybenzenethiol, 4-aminobenzenethiol, 4-acetamidobenzenethiol, 4-bromobenzenethiol, 4-methylbenzenethiol, N-acetyl-L-cysteine, and sodium 2-mercaptoethanesulfonate (MESNA).Various disulfides were inactive in vivo against cyanide poisoning.