A general synthesis of sulfenamides

✍ Scribed by David N. Harpp; Thomas G. Back

• Book ID: 104248465
• Publisher: Elsevier Science
• Year: 1971
• Tongue: French
• Weight: 153 KB
• Volume: 12
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)97598-7

✦ Synopsis

recently been shown that thiophthalimides (sulfenimides) (1) undergo displacement of phthalimide when treated with a variety of nucleophiles: thiols2, hydrodisulfides 2b , alkoxides 3 and phosphines 4 result in the formation of disulfides, trisulfides, sulfenate esters and N-alkylphthalimides. We wish to report that both primary and secondary amines also react with thiophthalimides to give excellent yields (81-100%) of the corresponding sulfenamides ( 2), (eq. I).